Pyridazin-3-one derivatives, their use, and intermediates for their production

ABSTRACT

Novel hydrazones of formula [2] having the following structural formula                    
     are provided, which are useful intermediates to form active ingredients of herbicides, wherein R 3  is hydrogen, alkyl, haloalkyl, or alkoxy alkyl; and Q is [Q-1], [Q-2], [Q-3], [Q-4] or [Q-5] as defined herein.

This is a divisional of application Ser. No. 09/011,269 filed Jan. 30, 1998, now U.S. Pat. No. 6,090,753 the disclosure of which is incorporated herein by reference which is a 371 of PCT/JP96/02311 filed Aug. 19, 1996.

TECHNICAL FIELD

The present invention relates to pyridazin-3-one derivatives, their use as herbicides, and intermediates for their production.

BACKGROUND ART

EP-A-0029123 discloses a process for the preparation of substituted anilines and novel substituted anilines. In particular, it teaches that certain substituted anilines obtained by this process are useful as important starting materials for the preparation of novel substituted pyridazin-3-one derivatives having herbicidal activity in postemergence application. These pyridazin-3-one derivatives are, however, different from those of the present invention in that they have a substituted phenoxyphenyl group as an essential structural element at position 2 of the pyridazinone ring and further have quite distinct substituents on the pyridazinone ring.

DISCLOSURE OF INVENTION

The present inventors have intensively studied to find a compound having excellent herbicidal activity. As a result, they have found that pyridazin-3-one derivatives represented by formula [1] as depicted below have excellent herbicidal activity, thereby completing the present invention.

Thus the present invention provides a compound of the formula:

wherein R¹ is C₁-C₃ haloalkyl; R² and R³ are the same or different and are hydrogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, or C₁-C₃ alkoxy C_(l)-C₃ alkyl; and Q is [Q-1], [Q-2], [Q-3], [Q-4], or [Q-5] of the formula:

wherein

X is hydrogen or halogen;

Y is halogen, nitro, cyano, or trifluoromethyl;

Z¹ is oxygen, sulfur, or NH;

Z² is oxygen or sulfur;

n is 0 or 1;

B is hydrogen, halogen, nitro, cyano, chlorosulfonyl, OR¹⁰, SR¹⁰, SO₂—OR¹⁰, N(R¹¹)R¹², SO₂N(R¹¹)R¹², NR¹¹(COR¹³), NR¹¹(SO₂R¹⁴), N(SO₂R¹⁴)—(SO₂R¹⁵), N(SO₂R¹⁴)(COR¹³), NHCOOR¹³, COOR¹⁰, CON(R¹¹)R¹², CSN(R¹¹)R¹², COR¹⁶, CR¹⁷═CR¹⁸COR¹⁶, CR¹⁷═CR¹⁸COOR¹³, CR¹⁷═CR¹⁸CON(R¹¹)R¹², CH₂CH—WCOOR¹³, CH₂CHWCON(R¹¹)R¹², CR¹⁷═NOR³³, CR₁₇═NN(R¹¹)R¹², CR¹⁷(Z²—R³⁴)₂, OCO₂R¹⁹, or OCOR¹⁹;

R⁴ is hydrogen or C₁-C₃ alkyl;

R⁵ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkylalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₃-C₈ alkoxyalkoxyalkyl, carboxy C₁-C₆ alkyl, (C₁-C₆ alkoxy)-carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxyl}carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl, CH₂CON(R¹¹)R¹², CH₂COON(R¹¹)R¹², CH(C₁-C₄ alkyl)CON(R¹¹)R¹², CH(C₁-C₄ alkyl)COON(R¹¹)R¹², C₂-C₈ alkylthioalkyl, or hydroxy C₁-C₆ alkyl;

R⁶ is C₁-C₆ alkyl, C₁-C₆ haloalkyl, formyl, cyano, carboxyl, hydroxy C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl, (C₁-C₆ alkyl)carbonyloxy C₁-C₆ alkyl, (C₁-C₆ haloalkyl)carbonyloxy C₁-C₆ alkyl, (C₁-C₆ alkoxy)carbonyl, or (C₁-C₆ alkyl)carbonyl;

R⁷ is hydrogen or C₁-C₆ alkyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, hydroxy C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, (C₁-C₅ alkyl)carbonyloxy C₁-C₆ alkyl, (C₁-C₆ haloalkyl)carbonyloxy C₁-C₆ alkyl, carboxyl, carboxy C₁-C₆ alkyl, (C₁-C₈ alkoxy)carbonyl, (C₁-C₆ haloalkoxy)carbonyl, (C₃-C₁₀ cycloalkoxy)carbonyl, (C₃-C₈ alkenyloxy)carbonyl, (C₃-C₈ alkynyloxy)carbonyl, aminocarbonyl, (C₁-C₆ alkyl)aminocarbonyl, di(C₁-C₆ alkyl)aminocarbonyl, (C₁-C₆ alkyl)aminocarbonyloxy C₁-C₆ alkyl, or di(C₁-C₆ alkyl)aminocarbonyloxy C₁-C₆ alkyl;

wherein R¹⁰ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, benzyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-C₈ alkylthioalkyl, carboxy C₁-C₆ alkyl, (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl, (C₁-C₆ haloalkoxy)carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl, (C₁-C₆ alkyl)carbonyl C₁-C₆ alkyl, (C₁-C₆ haloalkyl)carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkyl}carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkyl)carbonyl C₁-C₆ alkyl, CH₂CON—(R¹¹)R¹², CH₂COON(R¹¹)R¹², CH(C₁-C₄ alkyl)CON(R¹¹)R¹², CH(C₁-C₄ alkyl)—COON(R¹¹)R¹², {(C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl}oxycarbonyl C₁-C₆ alkyl, or hydroxy C₁-C₆ alkyl;

R¹¹ and R¹² are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, cyano C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-C₈ alkylthioalkyl, carboxy C₁-C₆ alkyl, (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl, or R¹¹ and R¹² are combined together to form tetramethylene, pentamethylene, or ethyleneoxy-ethylene;

R¹³ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, or C₃-C₆ alkenyl;

R¹⁴ and R¹⁵ are independently C₁-C₆ alkyl, C₁-C₆ haloalkyl, or phenyl optionally substituted with methyl or nitro;

R¹⁶ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C₂-C₈ alkoxyalkyl, or hydroxy C₁-C₆ alkyl;

R¹⁷ and R¹⁸ are independently hydrogen or C₁-C₆ alkyl;

R¹⁹ is C₁-C₆ alkyl;

R³³ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, or (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl;

R³⁴ is C₁-C₆ alkyl, or two R³⁴'s are combined together to form (CH₂)₂ or (CH₂)₃; and

W is hydrogen, chlorine, or bromine, (hereinafter referred to as the present compound(s)); and a herbicide containing it as an active ingredient.

The present invention also provides a compound of the formula:

wherein R³ is as defined above, and Q¹ is [Q¹-1], [Q-2], [Q¹-3], [Q-4], or [Q-5] of the formula:

wherein X, Y, Z¹, Z², n, R⁴, R⁵, R⁷, and R⁸ are as defined above; B¹ is hydrogen, halogen, nitro, cyano, OR²⁷, SR²⁷, SO₂OR²⁷, NR¹¹(R¹²), SO₂NR¹¹(R¹²), NR¹¹—(COR¹³), NR¹¹(SO₂R¹⁴), N(SO₂R¹⁴)(SO₂R¹⁵), N(SO₂R¹⁴)(COR¹³), NHCOOR¹³, COOR²⁷, CONR¹¹(R¹²), CSNR¹¹(R₁₂), CR¹⁷═CR¹⁸COOR¹³, CR¹⁷═CR¹⁸CONR¹¹—(R¹²), CH₂CHWCOOR¹³, CH₂CHWCONR¹¹(R¹²), CR¹⁷═NOR³³, CR¹⁷═NNR¹¹—(R¹²), CR¹⁷(Z²R³⁴)₂, OCO₂R¹⁹, or OCOR¹⁹; R⁹ is C₁-C₆ alkyl, C₁-C₆ haloalkyl, cyano, carboxyl, hydroxy C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkyl, C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl, (C₁-C₆ alkyl)carbonyloxy C₁-C₆ alkyl, (C₁-C₆ haloalkyl)carbonyloxy C₁-C₆ alkyl, (C₁-C₆ alkoxy)carbonyl, or (C₁-C₆ alkyl)carbonyl; wherein R¹⁹ is as defined above; R²⁷ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, benzyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-C₈ alkylthioalkyl, carboxy C₁-C₆ alkyl, (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl, (C₁-C₆ haloalkoxy)carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl, CH₂CON(R¹¹)R¹², CH₂COON(R¹¹)R¹², CH(C₁-C₄ alkyl)CON(R¹¹)R¹², CH(C₁-C₄ alkyl)COON(R¹¹)R¹², {(C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl}oxycarbonyl C₁-C₆ alkyl, or hydroxy C₁-C₆ alkyl; and R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁷, R¹⁸, R¹⁹, R³³, R³⁴, and Z² are as defined above.

In the above definition of the present compounds, the respective substituents are exemplified as follows:

Examples of the C₁-C₃ haloalkyl represented by R¹ include trifluoromethyl and chlorodifluoromethyl.

Examples of the C₁-C₃ alkyl represented by R² and R³ include methyl, ethyl, and isopropyl.

Examples of the C₁-C₃ haloalkyl represented by R² and R³ include trichloromethyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl.

Examples of the C₁-C₃ alkoxy C₁-C₃ alkyl represented by R² and R³ include methoxymethyl.

Examples of the halogen represented by X, Y, and B include chlorine, fluorine, bromine, or iodine.

Examples of the C₁-C₆ alkyl represented by R¹⁰ include methyl, ethyl, isopropyl, propyl, isobutyl, butyl, t-butyl, amyl, isoamyl, and t-amyl.

Examples of the C₁-C₆ haloalkyl represented by R¹⁰ include 2-chloroethyl, 3-chloropropyl, and 2,2,2-trifluoroethyl.

Examples of the C₃-C₈ cycloalkyl represented by R¹⁰ include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

Examples of the C₃-C₆ alkenyl represented by R¹⁰ include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

Examples of the C₃-C₆ haloalkenyl represented by R¹⁰ include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl.

Examples of the C₃-C₆ alkynyl represented by R¹⁰ include propargyl, 1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.

Examples of the C₃-C₆ haloalkynyl represented by R¹⁰ include 4-bromo-2-butynyl.

Examples of the cyano C₁-C₆ alkyl represented by R¹⁰ include cyanomethyl.

Examples of the C₂-C₈ alkoxyalkyl represented by R¹⁰ include methoxymethyl, methoxyethyl, ethoxymethyl, and ethoxyethyl.

Examples of the C₂-C₈ alkylthioalkyl represented by R¹⁰ include methylthiomethyl.

Examples of the carboxy C₁-C₆ alkyl represented by R¹⁰ include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl.

Examples of the (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl represented by R¹⁰ include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-amyloxycarbonylethyl.

Examples of the (C₁-C₆ haloalkoxy)carbonyl C₁-C₆ alkyl represented by R¹⁰ include 2-chloroethoxycarbonylmethyl.

Examples of the {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl represented by R¹⁰ include methoxymethoxycarbonylmethyl and 1-methoxymethoxycarbonylethyl.

Examples of the (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl represented by R¹⁰ include cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonylethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl.

Examples of the (C₁-C₆ alkyl)carbonyl C₁-C₆ alkyl represented by R¹⁰ include methylcarbonylmethyl.

Examples of the (C₁-C₆ haloalkyl)carbonyl C₁-C₆ alkyl represented by R¹⁰ include chloromethylcarbonylmethyl.

Examples of the {(C₁-C₄ alkoxy) C₁-C₄ alkyl}carbonyl C₁-C₆ alkyl represented by R¹⁰ include 2-methoxyethylcarbonylmethyl.

Examples of the (C₃-C₈ cycloalkyl)carbonyl C₁-C₆ alkyl represented by R¹⁰ include cyclopentylcarbonylmethyl.

Examples of the {(C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl}oxycarbonyl C₁-C₆ alkyl represented by R¹⁰ include (ethoxycarbonyl)methoxycarbonylmethyl.

Examples of the C₁-C₆ alkyl represented by R¹¹ and R¹² include methyl, ethyl, propyl, butyl, isopropyl, and isobutyl.

Examples of the C₁-C₆ haloalkyl represented by R¹¹ and R¹² include chloroethyl and bromoethyl.

Examples of the C₃-C₆ alkenyl represented by R¹¹ and R¹² include allyl, 1-methyl-2-propenyl, and 3-butenyl.

Examples of the C₃-C₆ alkynyl represented by R¹¹ and R¹² include propargyl and 1-methyl-2-propynyl.

Examples of the cyano C₁-C₆ alkyl represented by R¹¹ and R¹² include cyanomethyl.

Examples of the C₂-C₈ alkoxyalkyl represented by R¹¹ and R¹² include methoxymethyl and ethoxyethyl.

Examples of the C₂-C₈ alkylthioalkyl represented by R¹¹ and R¹² include methylthiomethyl and methylthioethyl.

Examples of the carboxy C₁-C₆ alkyl represented by R¹¹ and R¹² include carboxymethyl and 1-carboxyethyl.

Examples of the (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl represented by R¹¹ and R¹² include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-amyloxycarbonylethyl.

Examples of the (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl represented by R¹¹ and R¹² include cyclopentyloxycarbonylmethyl.

Examples of the {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl represented by R¹¹ and R¹² include methoxymethoxycarbonylmethyl and 1-methoxymethoxycarbonylethyl.

Examples of the C₁-C₆ alkyl represented by R¹³ include methyl, ethyl, propyl, butyl, amyl, isopropyl, isobutyl, and isoamyl.

Examples of the C₁-C₆ haloalkyl represented by R¹³ include 2,2,2-trifluoroethyl.

Examples of the C₃-C₈ cycloalkyl represented by R¹³ include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

Examples of the C₃-C₆ alkenyl represented by R¹³ include allyl.

Examples of the C₁-C₆ alkyl represented by R¹⁴ and R¹⁵ include methyl, ethyl, propyl, butyl, and isopropyl.

Examples of the C₁-C₆ haloalkyl represented by R¹⁴ and R¹⁵ include trifluoromethyl, 2,2,2-trifluoroethyl, 2-chloroethyl, chloromethyl, and trichloromethyl.

Examples of the phenyl optionally substituted by methyl or nitro, which is represented by R¹⁴ and R¹⁵, include phenyl, p-methylphenyl, 2-nitrophenyl, 3-nitrophenyl, and 4-nitrophenyl.

Examples of the C₁-C₆ alkyl represented by R¹⁶ include methyl, ethyl, propyl, butyl, amyl, isopropyl, isobutyl, t-butyl, isoamyl, and t-amyl.

Examples of the C₁-C₆ haloalkyl represented by R¹⁶ include chloromethyl, dichloromethyl, bromomethyl, dibromomethyl, 1-chloroethyl, 1,1-dichloroethyl, 1-bromoethyl, and 1,1-dibromoethyl.

Examples of the C₂-C₆ alkenyl represented by R¹⁶ include vinyl, allyl, 1-propenyl, and 1-methyl-2-propenyl.

Examples of the C₂-C₆ haloalkenyl represented by R¹⁶ include 3,3-dichloro-2-propenyl and 3,3-dibromo-2-propenyl.

Examples of the C₂-C₆ alkynyl represented by R¹⁶ include ethynyl and 2-butynyl.

Examples of the C₂-C₆ haloalkynyl represented by R¹⁶ include 3-bromo-2-propynyl.

Examples of the C₂-C₈ alkoxyalkyl represented by R¹⁶ include methoxymethyl, ethoxymethyl, and isopropoxymethyl.

Examples of the hydroxy C₁-C₆ alkyl represented by R¹⁶ include hydroxymethyl.

Examples of the C₁-C₆ alkyl represented by R¹⁷ and R¹⁸ include methyl.

Examples of the C₁-C₆ alkyl represented by R¹⁹ include methyl and ethyl.

Examples of the C₁-C₆ alkyl represented by R³³ include methyl and ethyl.

Examples of the C₁-C₆ haloalkyl represented by R³³ include 2-chloroethyl.

Examples of the C₃-C₈ cycloalkyl represented by R³³ include cyclopentyl.

Examples of the C₃-C₆ alkenyl represented by R³³ include allyl.

Examples of the C₃-C₆ haloalkenyl represented by R³³ include 2-chloro-2-propenyl.

Examples of the C₃-C₆ alkynyl represented by R³³ include propargyl.

Examples of the C₃-C₆ haloalkynyl represented by R³³ include 4-chloro-2-butynyl.

Examples of the cyano C₁-C₆ alkyl represented by R³³ include 2-cyanoethyl and cyanomethyl.

Examples of the (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl represented by R³³ include ethoxycarbonylmethyl.

Examples of the C₁-C₆ alkyl represented by R³⁴ include methyl and ethyl.

Examples of the C₁-C₃ alkyl represented by R⁴ include methyl.

Examples of the C₁-C₆ alkyl represented by R⁵ include methyl, ethyl, propyl, butyl, amyl, isopropyl, isobutyl, and isoamyl.

Examples of the C₁-C₆ haloalkyl represented by R⁵ include 2-chloroethyl, 2-bromoethyl, 3-chlorobutyl, 3-bromobutyl, difluoromethyl, and bromodifluoromethyl.

Examples of the C₃-C₈ cycloalkylalkyl represented by R⁵ include cyclopentylmethyl.

Examples of the C₃-C₆ alkenyl represented by R⁵ include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.

Examples of the C₃-C₆ haloalkenyl represented by R⁵ include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl.

Examples of the C₃-C₆ alkynyl represented by R⁵ include propargyl, 1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.

Examples of the C₃-C₆ haloalkynyl represented by R⁵ include 3-iodo-2-propynyl and 3-bromo-2-propynyl.

Examples of the cyano C₁-C₆ alkyl represented by R⁵ include cyanomethyl.

Examples of the C₂-C₈ alkoxyalkyl represented by R⁵ include methoxymethyl, ethoxymethyl, and 1-methoxyethyl.

Examples of the C₃-C₈ alkoxyalkoxyalkyl represented by R⁵ include methoxyethoxymethyl.

Examples of the carboxy C₁-C₆ alkyl represented by R⁵ include carboxymethyl, 1-carboxyethyl, and 2-carboxyethyl.

Examples of the (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl represented by R⁵ include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 1-amyloxycarbonylethyl, 1-isoamyloxycarbonylethyl, and 1-t-amyloxycarbonylethyl.

Examples of the {(C₁-C₄ alkoxy) C₁-C₄ alkoxy}carbonyl C₁-C₆ alkyl represented by R⁵ include methoxymethoxycarbonylmethyl and 1-methoxymethoxycarbonylethyl.

Examples of the (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl represented by R⁵ include cyclobutyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 1-cyclobutyloxycarbonylethyl, 1-cyclopentyloxycarbonylethyl, and 1-cyclohexyloxycarbonylethyl.

Examples of the C₂-C₈ alkylthioalkyl represented by R⁵ include methylthiomethyl.

Examples of the hydroxy C₁-C₆ alkyl represented by R⁵ include hydroxymethyl, hydroxyethyl, and hydroxypropyl.

Examples of the C₁-C₆ alkyl represented by R⁶ include methyl and ethyl.

Examples of the C₁-C₆ haloalkyl represented by R⁶ include bromomethyl, dibromomethyl, tribromomethyl, 1-bromoethyl, chloromethyl, dichloromethyl, and trichloromethyl.

Examples of the hydroxy C₁-C₆ alkyl represented by R⁶ include hydroxymethyl.

Examples of the C₁-C₆ alkoxy C₁-C₆ alkyl represented by R⁶ include methoxymethyl, ethoxymethyl, propoxymethyl, and isopropoxymethyl.

Examples of the C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl represented by R⁶ include methoxymethoxymethyl, methoxyethoxymethyl, and ethoxymethoxymethyl.

Examples of the (C₁-C₆ alkyl)carbonyloxy C₁-C₆ alkyl represented by R⁶ include acetyloxymethyl, ethylcarbonyloxymethyl, and isopropylcarbonyloxymethyl.

Examples of the (C₁-C₆ haloalkyl)carbonyloxy C₁-C₆ alkyl represented by R⁶ include trifluoroacetyloxymethyl, chloroacetyloxymethyl, and trichloroacetyloxymethyl.

Examples of the (C₁-C₆ alkoxy)carbonyl represented by R⁶ include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, amyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, and isoamyloxycarbonyl.

Examples of the (C₁-C₆ alkyl)carbonyl represented by R⁶ include methylcarbonyl, ethylcarbonyl, and isopropylcarbonyl.

Examples of the C₁-C₆ alkyl represented by R⁷ include methyl.

Examples of the C₁-C₆ alkyl represented by R⁸ include methyl and ethyl.

Examples of the C₁-C₆ haloalkyl represented by R⁸ include chloromethyl, bromomethyl, and fluoromethyl.

Examples of the C₁-C₆ hydroxyalkyl represented by R⁸ include hydroxymethyl.

Examples of the C₂-C₈ alkoxyalkyl represented by R⁸ include methoxymethyl, ethoxymethyl, isopropoxymethyl, butoxymethyl, and isobutoxymethyl.

Examples of the C₃-C₁₀ alkoxyalkoxyalkyl represented by R⁸ include methoxymethoxymethyl, methoxyethoxymethyl, and ethoxymethoxymethyl.

Examples of the (C₁-C₅ alkyl)carbonyloxy C₁-C₆ alkyl represented by R⁸ include acetyloxymethyl, ethylcarbonyloxymethyl, and isopropylcarbonyloxymethyl.

Examples of the (C₁-C₆ haloalkyl)carbonyloxy C₁-C₆ alkyl represented by R⁸ include 2-chloroethylcarbonyloxymethyl.

Examples of the carboxy C₁-C₆ alkyl represented by R⁸ include carboxymethyl.

Examples of the (C₁-C₈)alkoxycarbonyl represented by R⁸ include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, amyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, and isoamyloxycarbonyl.

Examples of the (C₁-C₆ haloalkoxy)carbonyl represented by R⁸ include 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 3-chlorobutoxycarbonyl, 1-chloro-2-propoxycarbonyl, 1,3-dichloro-2-propoxycarbonyl, 2,2-dichloroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, and 2,2,2-tribromoethoxycarbonyl.

Examples of the (C₃-C₁₀ cycloalkoxy)carbonyl represented by R⁸ include cyclobutyloxycarbonyl, cyclopentyloxycarbonyl, and cyclohexyloxycarbonyl.

Examples of the (C₃-C₈ alkenyloxy)carbonyl represented by R⁸ include allyloxycarbonyl and 3-butenyloxycarbonyl.

Examples of the (C₃-C₈ alkynyloxy)carbonyl represented by R⁸ include propargyloxycarbonyl, 3-butynyloxycarbonyl, and 1-methyl-2-propynyloxycarbonyl.

Examples of the (C₁-C₆ alkyl)aminocarbonyl represented by R⁸ include methylaminocarbonyl, ethylaminocarbonyl, and propylaminocarbonyl.

Examples of the di(C₁-C₆ alkyl)aminocarbonyl represented by R⁸ include dimethylaminocarbonyl, diethylaminocarbonyl, and diisopropylaminocarbonyl.

Examples of the (C₁-C₆ alkyl)aminocarbonyloxy C₁-C₆ alkyl represented by R⁸ include methylaminocarbonyloxymethyl, ethylaminocarbonyloxymethyl, and propylaminocarbonyloxymethyl.

Examples of the di(C₁-C₆ alkyl)aminocarbonyloxy C₁-C₆ alkyl represented by R⁸ include dimethylaminocarbonyloxyalkyl and diethylaminocarbonyloxyalkyl.

In the present compounds, preferred substituents from the viewpoint of their herbicidal activity are as follows:

R¹ is preferably methyl substituted with one or more fluorine atoms, such as trifluoromethyl or chlorodifluoromethyl, or ethyl substituted with one or more fluorine atoms, such as pentafluoroethyl, and more preferably trifluoromethyl;

R² is preferably C₁-C₃ alkyl such as methyl or ethyl, or hydrogen, and more preferably methyl or hydrogen;

R³ is preferably C₁-C₃ alkyl such as methyl or ethyl, or hydrogen, and more preferably methyl or hydrogen; and

Q is preferably [Q-1], [Q-2], [Q-3], or [Q-4].

Preferred examples of the present compounds from the viewpoint of their herbicidal activity are those which contain the above preferred substituents in combination.

When Q is [Q-1], more preferred compounds are those wherein X is hydrogen or fluorine and Y is chlorine. Among these compounds are more preferred ones wherein B is OR¹⁰, SR¹⁰, N(R¹¹)R¹², NR¹¹(SO₂R¹⁴), or COOR¹⁰. Among these compounds are more preferred ones wherein R¹⁰ is C₁-C₆ alkyl, C₃-C₆ alkynyl, (C₁-C₈ alkoxy)carbonyl C₁-C₆ alkyl, or (C₃-C₈ cycloalkoxy)carbonyl C₁-C₆ alkyl; R¹¹ is hydrogen; R¹² is (C₁-C₆ alkoxy)carbonyl C₁-C₆ alkyl; and R¹⁴ is C₁-C₆ alkyl or C₁-C₆ haloalkyl.

When Q is [Q-2], more preferred compounds are those wherein X is fluorine or hydrogen; Z¹ is oxygen; R⁴ is hydrogen; and n is 1. Among these compounds are more preferred ones wherein R⁵ is C₃-C₆ alkynyl.

Typical examples of the preferred compounds are as follows:

7-Fluoro-6-(5-trifluoromethyl-3-pyridazinon -2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;

7-Fluoro-6-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;

6-(5-Trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;

6-(4-Methy-1-5-trifluoromethyl -3-pyridazinon-2-yl )-4-propargyl-2H-1,4-benzoxazin-3-one;

2-(4-Chloro-2-fluoro-5-isopropoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one;

2-(4-Chloro-2-fluoro-5-methoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one;

2-(4-Chloro-2-fluoro-5-ethoxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one;

2-(4-Chloro-2-fluoro-5-propargyloxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one;

Methyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;

Ethyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;

Propyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;

Isopropyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;

Butyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;

Pentyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;

Cyclopentyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;

Ethyl 2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate;

Methyl 2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate;

Ethyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate;

Methyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate;

Ethyl 2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate;

Methyl 2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate;

Methyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate;

Ethyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenoxy}propionate;

Ethyl 2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate;

Methyl 2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthioacetate;

Ethyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate;

Methyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate;

Isopropyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate;

Ethyl 2-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenylamino}propionate;

Ethyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylamino}propionate;

N-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl}methanesulfonamide;

N-{2-chloro-4-fluoro-5-(4-methyl -5-trifluoromethyl-3-pyridazinon-2-yl)phenyl}chloromethanesulfonamide;

N-{2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl}methanesulfonamide;

Methyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate;

Ethyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate;

Ethyl 2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate;

Isopropyl 2-chloro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate; and

2-(4-Chloro-2-fluoro-5-propargyloxyphenyl)-6-methyl-5-trifluoromethylpyridazin-3-one.

Among these compounds, more preferred ones from the viewpoint of their herbicidal activity are as follows:

7-Fluoro-6-(5-trifluoromethyl-3-pyridazinon-2-yl)-4-proparygyl-2H-1,4-benzoxazin-3-one;

7-Fluoro-6-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;

6-(4-Methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one;

Ethyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyrizazinon-2-yl)phenoxy}propionate; and

Ethyl 2-{2-chloro-4-fluoro-5-(5-trifluoromethyl-3-pyridazinon-2-yl)phenylthio}propionate.

In addition, more preferred ones from the viewpoint of their selectivity between crop plants and undesired weeds are as follows:

2-(4-Chloro-2-fluoro-5-propargyloxyphenyl)-4-methyl-5-trifluoromethylpyrizazin-3-one;

Ethyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenoxyacetate;

N-{2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)phenyl}methanesulfonamide; and

Ethyl 2-chloro-4-fluoro-5-(4-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)benzoate.

The present compounds can be produced, for example, according to the production processes described below.

(Production Process 1)

This is the production process in which among the present compounds, a compound of the formula:

wherein R¹, R², R³, and Q¹ are as defined above, is produced by reacting a hydrazone derivative of the formula:

wherein R¹, R³, and Q¹ are as defined above, with a compound of the formula:

wherein R² is as defined above; R²⁸ is C₁-C₆ alkyl such as methyl or ethyl; and Ar is an optionally substituted phenyl such as phenyl.

The reaction is usually effected in a solvent. The reaction temperature is usually in the range of −20° to 150° C., preferably 0° to 100° C. The reaction time is usually in the range of a moment to 72 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of compound [5] to 1 mole of compound [4] is ideal, can be freely changed depending upon the reaction conditions.

Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran (THF), and ethylene glycol dimethyl ether; nitro compounds such as nitromethane and nitrobenzene; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; water; and mixtures thereof.

After completion of the reaction, the reaction solvent is distilled out from the reaction mixture and the residue is subjected to chromatography, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as chromatography or recrystallization. Thus the desired compound of the present invention can be isolated.

The above reaction is effected through a compound of the formula:

wherein R¹, R², R³, R²⁸, and Q¹ are as defined above.

This production process can also be conducted by isolating compound [6] and effecting intramolecular cyclization of compound [6]. The cyclization can usually be effected in a solvent. The reaction temperature is usually in the range of −20° to 150° C., preferably 50° to 150° C. The reaction time is usually in the range of a moment to 72 hours.

Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitrites such as acetonitrile and isobutyronitrile; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; fatty acids such as formic acid, acetic acid, and propionic acid; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; water; and mixtures thereof.

As the reaction catalyst, acids such as sulfuric acid or bases such as sodium methylate can be used.

(Production Process 2)

This is the production process according to the following scheme:

wherein R⁵¹ is a substituent other than hydrogen, which is included in the definition of R⁵; R¹, R², R³, R⁴, and X are as defined above; R²² is C₁-C₆ alkyl; and D is chlorine, bromine, iodine, methanesulfonyloxy, trifluoromethanesulfonyloxy, or p-toluenesulfonyloxy.

Process For Producing Compound [8] From Compound [7]

Compound [8] can be produced by reacting compound [7] with a nitrating agent in a solvent.

Nitrating agent: nitric acid or the like

Amount of nitrating agent: 1 to 10 moles per mole of compound [7]

Solvent: sulfuric acid

Temperature: −10° C. to room temperature

Time: a moment to 24 hours

Process For Producing Compound [9] From Compound [8]

Compound [9] can be produced by reacting compound [8] with a compound of the formula:

wherein R⁴ and R²² are as defined above, in the presence of potassium fluoride in a solvent.

Amount of compound [12]: 1 to 50 moles per mole of compound [8]

Amount of potassium fluoride: 1 to 50 moles per mole of compound [8]

Solvent: 1,4-dioxane or the like

Temperature: room temperature to refluxing temperature under heating

Time: a moment to 96 hours

Process For Producing Compound [10] From Compound [9]

Compound [10] can be produced by reducing compound [9] with iron powder or the like in the presence of an acid in a solvent.

Amount of iron powder: 3 moles to an excess per mole of compound [9]

Acid: acetic acid or the like

Amount of acid: 1 to 10 moles

Solvent: water, ethyl acetate, or the like

Temperature: room temperature to refluxing temperature under heating

Time: a moment to 24 hours

Process For Producing Compound [11] From Compound [10]

Compound [11] can be produced by reacting compound [10] with a compound of the formula:

 R⁵¹—D  [13]

wherein R⁵¹ and D are as defined above.

The reaction is usually effected in the presence of a base in a solvent. The reaction temperature is usually in the range of −20° to 150° C., preferably 0° to 50° C. The reaction time is usually in the range of a moment to 48 hours. The amounts of the reagents to be used in the reaction are usually 1 to 3 moles of compound [13] and usually 1 to 2 moles of the base, per mole of compound [10].

Examples of the base which can be used include inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate, and sodium carbonate; and organic bases such as triethylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, N,N-dimethylaniline, and N,N-diethylaniline.

Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; nitro compounds such as nitrobenzene; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylamine, N,N-diethylaniline, and N-methylmorpholine; and mixtures thereof.

After completion of the reaction, the reaction mixture is poured into water, if necessary, and subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the present compound [11] can be obtained.

The above compound [9] can also be produced according to the following scheme:

wherein R¹, R², R³, R⁴, R²², and X are as defined above.

Process For Producing Compound [15] From Compound [14]

Compound [15] can be produced by reacting compound [14] with a compound of the formula:

wherein R⁴ and R²² are as defined above, in the presence of a base in a solvent.

Amount of compound [17]: 1 to 2 moles per mole of compound [14]

Base: sodium hydride, sodium carbonate, or the like

Amount of base: 1 to 2 moles per mole of compound [14]

Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

Temperature: 0° to 100° C.

Time: a moment to 24 hours

Process For Producing Compound [9] From Compound [15]

Compound [9] can be produced by reacting compound [15] with a nitrating agent in a solvent.

Nitrating agent: nitric acid or the like

Amount of nitrating agent: 1 to 10 moles per mole of compound [15]

Solvent: sulfuric acid, acetic acid, or the like

Temperature: −10° C. to room temperature

Time: a moment to 24 hours

Process For Producing Compound [16] From Compound [14]

Compound [16] can be produced by reacting compound [14] with a nitrating agent in a solvent.

Nitrating agent: nitric acid or the like

Amount of nitrating agent: 1 to 10 moles per mole of compound [14]

Solvent: sulfuric acid, acetic acid, or the like

Temperature: −10° C. to room temperature

Time: a moment to 24 hours

Process For Producing Compound [9] From Compound [16]

Compound [9] can be produced by reacting compound [16] with compound[17] in the presence of a base in a solvent.

Amount of compound [17]: 1 to 2 moles per mole of compound [16]

Base: sodium hydride, potassium carbonate, or the like

Amount of base: 1 to 2 moles per mole of compound [16]

Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

Temperature: 0° to 100° C.

Time: a moment to 24 hours

(Production Process 3)

This is the production process according to the following scheme:

wherein X, R¹, R², R³, R⁵¹, and D are as defined above.

Process For Producing Compound [19] From Compound [18]

Compound [19] can be produced by reducing compound [18] with iron powder or the like in the presence of an acid in a solvent.

Amount of iron powder: 3 moles to an excess per mole of compound [18]

Acid: acetic acid or the like

Amount of acid: 1 to 10 moles per mole of compound [18]

Solvent: water, ethyl acetate, or the like

Temperature: room temperature to refluxing temperature under heating

Time: a moment to 24 hours

Process For Producing Compound [21] From Compound [20]

Compound [20] can be produced by reacting compound [19] with sodium thiocyanate, potassium thiocyanate, or the like in a solvent, and then reacting it with bromine or chlorine in a solvent.

Amount of sodium thiocyanate, potassium thiocyanate, or the like: 1 to 10 moles per mole of compound [19]

Amount of bromine or chlorine: 1 to 10 moles per mole of compound [19]

Solvent: aqueous hydrochloric acid, aqueous acetic acid, aqueous sulfuric acid, or the like

Temperature: 0° to 50° C.

Time: a moment to 150 hours

Process For Producing Compound [21] From Compound [20]

Compound [21] can be produced by 1) reacting compound [20] with sodium nitrite, potassium nitrite, or the like in a solvent, and then 2) heating it in an acidic solution.

<Reaction 1)>

Amount of sodium nitrite, potassium nitrite, or the like: 1 to 2 moles per mole of compound [20]

Solvent: aqueous hydrochloric acid or aqueous sulfuric acid

Temperature: −10° to 10° C.

Time: a moment to 5 hours

<Reaction 2)>

Acidic solution: aqueous hydrochloric acid, aqueous sulfuric acid, or the like

Temperature: 70° C. to refluxing temperature under heating

Time: a moment to 24 hours

Process For Producing Compound [22] From Compound [21]

Compound [22] can be produced by reacting compound [21] with compound [13] in the presence of a base in a solvent.

Amount of compound [13]: 1 to 3 moles per mole of compound [21]

Base: sodium hydride, potassium carbonate, or the like

Amount of base: 1 to 2 moles per mole of compound [21]

Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

Temperature: 0° to 100° C.

Time: a moment to 48 hours

(Production Process 4)

This is the production process according to the following scheme:

wherein X, R¹, R², R³, and R⁵ are as defined above.

Process For Producing Compound [24] From Compound [23]

Compound [24] can be produced by reducing compound [23] with iron powder or the like in the presence of an acid in a solvent.

Amount of iron powder: 3 moles to an excess per mole of compound [23]

Acid: acetic acid or the like

Amount of acid: 1 to 10 moles per mole of compound [23]

Solvent: water, ethyl acetate, or the like

Temperature: room temperature to refluxing temperature under heating

Time: a moment to 24 hours

Process For Producing Compound [25] From Compound [24]

Compound [25] can be produced by 1) reacting compound [24] with a nitrite salt in a solvent to form a diazonium salt, and then 2) raising the temperature to cause the cyclization of the diazonium salt in a solvent.

<Reaction 1)>

Nitrite salt: sodium nitrite, potassium nitrite, or the like

Amount of nitrite salt: 1 to 2 moles per mole of compound [24]

Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or the like

Temperature: −10° to 10° C.

Time: a moment to 5 hours

<Reaction 2)>

Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or the like

Temperature: room temperature to 80° C.

Time: a moment to 24 hours

(Production Process 5)

This is the production process according to the following scheme:

wherein Y¹ is a substituent other than nitro, which is included in the definition of Y;

R¹⁰¹ is a substituent other than hydrogen, which is included in the definition of R¹⁰; and

X, R¹, R², and R³ are as defined above.

Process For Producing Compound [27] From compound [26]

Compound [27] can be produced by adding nitric acid to compound [26] in a solvent (see Organic Synthesis Collective, Vol. 1, p. 372).

The reaction temperature is usually in the range of 0° to 100° C. The reaction time is usually in the range of a moment to 24 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of nitric acid to 1 mole of compound [26] is ideal, can be freely changed depending upon the reaction conditions.

Examples of the solvent which can be used include acidic solvents such as sulfuric acid.

Process For Producing Compound [28] From compound [27]

Compound [28] can be produced by reducing compound [27] in a solvent (see Organic Synthesis Collective, Vol. 2, p. 471, and ibid., Vol. 5, p. 829).

For example, the production can be achieved by adding compound [27], which is neat or dissolved in a solvent such as ethyl acetate, to a mixture of acetic acid, iron powder, and water. The reaction temperature is usually in the range of 0° to 100° C. The reaction time is usually in the range of a moment to 24 hours.

After completion of the reaction, the reaction mixture is filtered to collect the crystals, which may be precipitated by the addition of water, if necessary, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired product can be isolated.

Process For Producing Compound [29] From compound [28]

Compound [29] can be produced by 1) reacting compound [28] with a nitrite salt in a solvent, and then 2) heating it in an acidic solvent.

<Reaction 1)>

Nitrite salt: sodium nitrite, potassium nitrite, or the like

Amount of nitrite salt: 1 to 2 moles per mole of compound [28]

Solvent: aqueous hydrochloric acid, aqueous sulfuric acid, or the like

Temperature: −10° to 10° C.

Time: a moment to 5 hours

<Reaction 2)>

Acidic solvent: aqueous hydrochloric acid or aqueous sulfuric acid

Temperature: 70° C. to refluxing temperature under heating

Time: a moment to 24 hours.

Process For Producing Compound [30] From Compound [29]

Compound [30] can be produced by reacting compound [29] with a compound of the formula:

R¹⁰¹—D  [31]

wherein R¹⁰¹ and D are as defined above, in the presence of a base in a solvent.

The reaction is usually effected in a solvent. The reaction temperature is usually in the range of −20° to 150° C., preferably 0° to 100° C. The reaction time is usually in the range of a moment to 72 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of compound [31] and 1 mole of a base to 1 mole of compound [29] is ideal, can be freely changed depending upon the reaction conditions.

Examples of the base which can be used include organic bases and inorganic bases such as potassium carbonate, sodium hydroxide, and sodium hydride.

Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitrites such as acetonitrile and isobutyronitrile; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof.

After completion of the reaction, the reaction mixture is filtered to collect the crystals, which may be precipitated by the addition of water, if necessary, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired product can be isolated.

(Production Process 6)

This is the production process according to the following scheme:

wherein R²³ and R²⁴ are independently a substituent other than hydrogen, which is included in the definition of R¹¹ and R¹²; or COR¹³, SO₂R¹⁴, SO₂R¹⁵, or COOR¹⁰, wherein R¹⁰, R¹³, R¹⁴, and R¹⁵ are as defined above; X, Y¹, R¹, R², and R³ are as defined above.

Process For Producing compound [32] From Compound [28]

Compound [32] can be produced by reacting compound [28] with a compound of the formula:

R²⁰—D  [34]

wherein R²⁰ is a substituent other than hydrogen, which is included in the definition of R¹¹ or R¹²; or COR¹³, SO₂R¹⁴, SO₂R¹⁵, or COOR¹⁰, wherein R¹⁰, R¹³, R¹⁴, and R¹⁵ are as defined above; and D is as defined above; or with a compound of the formula:

(R²¹)₂O  [35]

wherein R²¹ is COR¹³, SO₂R¹⁴, SO₂R¹⁵, or COOR¹⁰, wherein R¹⁰, R¹³, R¹⁴, and R¹⁵ are as defined above, usually in the presence of a base and usually in a solvent.

The reaction temperature is usually in the range of −20° to 200° C., preferably 0° to 180° C. The reaction time is usually in the range of a moment to 72 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of compound [34] or [35] to 1 mole of compound [28] is ideal, can be freely changed depending upon the reaction conditions.

Examples of the base which can be used include organic bases such as pyridine and triethylamine, and inorganic bases.

Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitrites such as acetonitrile and isobutyronitrile; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof.

After completion of the reaction, the reaction mixture is filtered to collect the precipitated crystals, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired product can be isolated.

Process For Producing Compound [33] From Compound [32]

Compound [33] can be produced by reacting compound [32] with compound [34] or [35]. This production process is based on the process for producing compound [32] from compound [28].

(Production Process 7)

This is the production process according to the following scheme:

wherein X, Y, R¹, R², R³, R¹⁰, R¹¹, and R¹² are as defined above.

Process For Producing Compound [37] From Compound [36]

Compound [37] can be produced by reacting compound [36] with chlorosulfonic acid without any solvent or in a solvent.

Amount of chlorosulfonic acid: 1 mole to an excess per mole of compound [36]

Solvent: sulfuric acid

Temperature: 0° to 70° C.

Time: a moment to 24 hours

(see Org. Syn. Coll., Vol. 1, 8 (1941))

Process For Producing Compound [38] From Compound [37]

Compound [38] can be produced by reacting compound [37] with a compound of the formula:

R¹⁰—OH  [40]

wherein R¹⁰ is as defined above, in the presence of a base without any solvent or in a solvent.

Amount of compound [24]: 1 mole to an excess per mole of compound [37]

Base: organic bases such as triethylamine or inorganic bases such as potassium carbonate

Amount of base: 1 to 2 moles per mole of compound [37]

Solvent: N,N-dimethylformamide, 1,4-dioxane, or the like

Temperature: 0° to 100° C.

Time: a moment to 24 hours

Process For Producing Compound [39] From Compound [37]

Compound [39] can be produced by reacting compound [37] with a compound of the formula:

 R¹¹R¹²NH  [41]

wherein R¹¹ and R¹² are as defined above, in the presence or absence of a base without any solvent or in a solvent.

Amount of compound [41]: 1 mole to an excess per mole of compound [37]

Base: organic bases such as triethylamine or inorganic bases such as potassium carbonate

Amount of base: 1 to 2 moles per mole of compound [37]

Solvent: 1,4-dioxane, N,N-dimethylformamide, or the like

Temperature: 0° to 100° C.

Time: a moment to 24 hours

(Production Process 8)

This is the production process according to the following scheme:

wherein X, Y, R¹, R², R³, R¹¹, R¹², R¹⁷, R¹⁸, and R²² are as defined above.

Process For Producing Compound [43] From Compound [42]

Compound [43] can be produced from compound [42] according to the method described in JP-A5-294920/1993, pp. 15-16.

Process For Producing Compound [44] From Compound [43]

Compound [44] can be produced by reacting compound [43] with a compound of the formula:

(C₆H₅)₃P═CR¹⁸COOR²²  [45]

or

(C₂H₅O)₂P(O)CHR¹⁸COOR²²  [46]

wherein R¹⁸ and R²² are as defined above, in a solvent, and when compound [46] is used, in the presence of a base.

Amount of compound [45] or [46]: 1 to 2 moles per mole of compound [43]

Solvent: tetrahydrofuran, toluene, or the like

Base: sodium hydride or the like

Amount of base: 1 to 2 moles per mole of compound [43]

Temperature: 0° to 50° C.

Time: a moment to 24 hours

Process For Producing Compound [45] From Compound [44]

Compound[45] can be produced by reacting compound [44] with compound [41].

(Production Process 9)

This is the production process according to the following scheme:

wherein W² is chlorine or bromine; and X, Y, R¹, R², R³, and R¹³ are as defined above.

The reaction conditions are described, for example, in U.S. Pat. No. 5,208,212.

The production can be achieved by converting compound [48] into a diazonium salt in a solution of hydrochloric acid, hydrobromic acid, or the like according to the ordinary method, and then reacting it with a compound of the formula:

CH₂═CHCO₂R¹³  [50]

wherein R¹³ is as defined above, in the presence of a copper salt, such as copper (II) chloride or copper (II) bromide, in a solvent such as acetonitrile.

The reaction temperature is usually in the range of −20° to 150° C., preferably 0° to 60° C. The reaction time is usually in the range of a moment to 72 hours.

After completion of the reaction, the reaction mixture is filtered to collect the crystals, which may be precipitated by the addition of water, if necessary, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired product can be isolated.

(Production Process 10)

This is the production process according to the following scheme:

wherein W³ is bromine or iodine; and X, Y¹, R¹, R², R³, and R¹³ are as defined above.

Process For Producing Compound [51] From Compound [28]

Compound [51] can be produced by 1) making a diazonium salt from compound [28] in a solvent and then 2) reacting it with potassium iodide or copper (I) bromide in a solvent.

<Reaction 1)>

Diazotizing agent: sodium nitrite, potassium nitrite, or the like.

Amount of diazotizing agent: 1 to 2 moles per mole of compound [28]

Solvent: aqueous hydrogen bromide, aqueous sulfuric acid, or the like.

Temperature: −10° to 10° C.

Time: a moment to 5 hours

<Reaction 2)>

Amount of potassium iodide or copper (I) bromide: 1 mole to an excess per mole of compound [28]

Solvent: aqueous hydrogen bromide, aqueous sulfuric acid, or the like

Temperature: 0° to 80° C.

Time: a moment to 24 hours

(see Org. Syn. Coll., Vol. 2, 604 (1943), and ibid., Vol. 1, 136 (1941))

Process For Producing Compound [52] From Compound [51]

Compound [52] can be produced by reacting compound [51] with a compound of the formula:

R¹³—OH  [53]

wherein R¹³ is as defined above, in the presence of a transition metal catalyst and a base in a solvent under an atmosphere of carbon monoxide.

Catalyst: PdCl₂(PPh₃)₂ or the like

Amount of catalyst: a catalytic amount to 0.5 mole per mole of compound [51]

Amount of compound [53]: 1 mole to an excess per mole of compound [51]

Base: organic bases such as diethylamine

Amount of base: 1 to 2 moles per mole of compound [51]

Solvent: N,N-dimethylformamide or the like

Pressure of carbon monoxide: 1 to 150 atm.

Temperature: 0° to 100° C.

Time: a moment to 72 hours

(see Bull. Chem. Soc. Jpn., 48 (7) 2075 (1975))

(Production Process 11)

This is the production process according to the following scheme:

wherein X, Y, R¹, R², R³, and R¹⁹ are as defined above.

Compound [55] can be produced by hydrolyzing compound [54] in an acid solvent such as sulfuric acid, or in the presence of an acid such as boron tribromide in a solvent such as methylene chloride.

The reaction temperature is usually in the range of −20° to 150° C., preferably 0° to 100° C. The reaction time is usually in the range of a moment to 72 hours.

The amount of the acid to be used in the reaction, although the proportion of 1 mole of the acid to 1 mole of compound [54] is ideal, can be freely changed depending upon the reaction conditions.

After completion of the reaction, the reaction mixture is filtered to collect the crystals, which may be precipitated by the addition of water, if necessary, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired product can be isolated.

(Production Process 12)

This is the production process according to the following scheme:

wherein X, Y, R¹, R², R³, Z², and R¹⁷ are as defined above; Z³ is oxygen or sulfur; R²⁵ is hydrogen or C₁-C₅ alkyl; and R²⁶ is C₁-C₆ alkyl C₃-C₆ alkenyl, or C₃-C₆ alkynyl.

Compound [57] can be produced by reacting compound [56] with a compound of the formula:

R²⁶Z³H  [58]

wherein R²⁶ and Z³ are as defined above, in the presence or absence of a catalyst and usually in a solvent.

The amount of compound [58] to be used in the reaction, although the proportion of 1 mole of compound [58] to 1 mole of compound [56] is ideal, can be freely changed depending upon the reaction conditions.

Examples of the catalyst which can be used include p-toluenesulfonic acid. Examples of the solvent which can be used include toluene, xylene or the like, or compound [56].

The reaction temperature is usually in the range of 0° to 200° C., preferably 50° to 150° C. The reaction time is usually in the range of a moment to 72 hours.

After completion of the reaction, the reaction mixture is filtered to collect the crystals, which may be precipitated by the addition of water, if necessary, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired product can be isolated.

(Production Process 13)

This is the production process according to the following scheme:

wherein R⁶¹ is a substituent other than methyl, which is included in the definition of R⁶; and X, Y, R¹, R², and R³ are as defined above.

Process For Producing Compound [59] From Compound [55]

Compound [59] can be produced by reacting compound [55] with 2,3-dichloropropene in the presence of a base in a solvent.

Amount of 2,3-dichloropropene: 1 to 3 moles per mole compound [55]

Base: inorganic bases such as potassium carbonate

Amount of base: 1 to 2 moles per mole of compound [55]

Solvent: N,N-dimethylformamide or the like

Temperature: 0° to 70° C.

Time: a moment to 24 hours

Process For Producing Compound [60] From Compound [59]

Compound [60] can be produced by heating compound [59] in a solvent.

Solvent: N,N-dimethylformamide, N,N-dimethylaniline, N,N-diethylaniline, p-diisopropylbenzene, or the like

Temperature: 70° to 200° C.

Time: a moment to 24 hours

Process For Producing Compound [61] From Compound [60]

Compound [61] can be produced from compound [62] according to the method in which the methyl group in position 2 on the benzofuran ring is replaced with another substituent, as described in U.S. Pat. No. 5,308,829, columns 2-11.

(Production Process 14)

This is the production process according to the following scheme:

wherein X, Y, R¹, R², R³, and R⁷ are as defined above.

Process For Producing Compound [62] From compound [55]

Compound [62] can be produced by reacting compound [55] with a compound of the formula:

 CH₂═CR⁷CH₂W²  [65]

wherein W² and R⁷ are as defined above, in the presence of a base in a solvent.

Amount of compound [65]: 1 to 5 moles per mole of compound [55]

Base: inorganic bases such as potassium carbonate

Amount of base: 1 to 2 moles per mole of compound [55]

Solvent: N,N-dimethylformamide, 1,4-dioxane, or the like

Temperature: 0° to 70° C.

Time: a moment to 24 hours

Process For Producing Compound [63] From Compound [62]

Compound [64] can be produced by heating compound [62] in a solvent.

Solvent: N,N-dimethylaniline, N,N-diethylaniline, p-diisopropylbenzene, or the like

Temperature: 100° to 200° C.

Time: a moment to 24 hours

Process For Producing Compound [64] From Compound [63]

Compound [64] can be produced by heating compound [63] in the presence of an acid in a solvent.

Acid: organic acids such as p-toluenesulfonic acid; and inorganic acids such as sulfuric acid

Amount of acid: a catalytic amount to 1 mole per mole of compound [63]

Solvent: toluene, xylene, or the like

Temperature: 100° to 250° C.

Time: a moment to 24 hours

(Production Process 15)

This is the production process according to the following scheme:

wherein R⁸¹ is a substituent other than methyl and hydroxymethyl, which is included in the definition of R⁸; and X, Y, R¹, R², R³, and R⁷ are as defined above.

Process For Producing Compound [66] From Compound [63]

Compound [66] can be produced by reacting compound [63] with a peracid in a solvent.

Peracid: m-chloroperbenzoic acid or peracetic acid

Amount of peracid: 1 mole to an excess per mole of compound [63]

Solvent: halogenated hydrocarbons such as dichloromethane; and organic acids such as acetic acid

Temperature: −20° C. to room temperature

Time: a moment to 24 hours

Process For Producing Compound [67] From Compound [66]

Compound [67] can be produced by reacting compound [66] in the presence of a base in a solvent.

Base: potassium carbonate or the like

Amount of base: 1 to 2 moles per mole of compound [66]

Solvent: methanol, ethanol, or the like

Temperature: 0° to 50° C.

Time: a moment to 5 hours

Process For Producing Compound [68] From Compound [67]

Compound [68] can be produced from compound [67] according to the method in which the hydroxyalkyl group in position 2 on the dihydrobenzofuran ring is replaced with another substituent, as described in U.S. Pat. No. 5,411,935, columns 5-10.

(Production Process 16)

This is the production process according to the following scheme:

wherein W¹ is halogen, preferably chlorine; R³² is hydrogen or C₁-C₅ alkyl; and X, Y, Z², R¹, R², R³, R¹¹, R¹², R³³, and R³⁴ are as defined above.

Process For Producing Compound [69] From compound [42]

Compound [69] can be produced by reacting compound [42] with a halogenating agent such as thionyl chloride in a solvent according to the ordinary method.

Process For Producing Compound [70] From Compound [69]

Compound [70] can be produced by reacting compound [69] with a compound of the formula:

wherein M^(⊕) is an alkali metal cation, preferably lithium cation or sodium cation; and R¹⁹, R²², and R³² are as defined above, to give a compound of the formula:

wherein X, Y, R¹, R², R³, R¹⁹, R²², and R³² are as defined above, and then hydrolyzing and decarboxylating compound [75].

The first reaction is usually effected in a solvent. The reaction temperature is usually in the range of −20° to 50° C., preferably room temperature. The reaction time is usually in the range of a moment to 72 hours.

Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; acid amides such as formamide, N,N-dimethylformamide, and acetamide; sulfur compounds such as dimethylsulfoxide and sulforane; and mixtures thereof.

The second reaction is effected in the presence of sulfuric acid, hydrobromic acid, or the like in a solvent such as a lower carboxylic acid, e.g., acetic acid, or without any solvent. The reaction temperature is usually in the range of 80° to 140° C., preferably 100° to 120° C. The reaction time is usually in the range of a moment to 72 hours.

Process For Producing Compound [71] From Compound [70]

Compound [71] can be produced by reacting compound [70] with a compound of the formula:

H₂N—O—R³³  [76]

wherein R³³ is as defined above.

The reaction is effected in a lower alcohol such as methanol, ethanol or isopropanol, or in a mixed solution of such a lower alcohol and water. The reaction temperature is in the range of 0° to 80° C. The reaction time is in the range of a moment to 72 hours.

Compound [76] can be used in the form of a free base or an acid addition salt such as a hydrochloride salt or a sulfate salt.

The above reaction can also be effected with the addition of a basic catalyst such as an organic base, e.g., pyridine; an alkali metal carbonate, e.g., sodium carbonate, potassium carbonate or the like; alkali metal hydrogencarbonate; or alkaline earth metal carbonate.

Compound [71] can also be produced by reacting a compound of the formula:

wherein X, Y, R¹, R², R³, and R³² are as defined above, with a compound of the formula:

 R³³—D  [78]

wherein R³³ and D are as defined above, in the presence of a base, usually in a solvent.

Examples of the base which can be used include alkali metal alcoholates and alkali metal hydrides such as sodium hydride.

The amounts of the reagents to be used in the reaction, although the proportion of about 1 mole of compound [78] and 1 to 2 moles of the base to 1 mole of compound [77] is ideal, can be free changed depending upon the reaction conditions.

Examples of the solvent which can be used include ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; acid amides such as formamide, N,N-dimethylformamide, and acetamide; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; and mixtures thereof.

The reaction temperature in the above reaction is in the range of −10° to 100° C., preferably 0° to 80° C. The reaction time is in the range of a moment to 72 hours.

Process For Producing Compound [72] From compound [70]

Compound [72] can be produced by reacting compound [70] with a compound of the formula:

wherein R¹¹ and R¹² are as defined above.

The reaction is effected in a lower alcohol such as methanol, ethanol or isopropanol, or in a mixed solution of such a lower alcohol and water. The reaction temperature is in the range of 0° to 80° C. The reaction time is in the range of a moment to 72 hours.

Compound [79] can be used in the form of a free base or an acid addition salt such as a hydrochloride salt or a sulfate salt.

The above reaction can also be effected with the addition of a basic catalyst such as an organic base, e.g., pyridine; an alkali metal carbonate, e.g., sodium carbonate, potassium carbonate or the like; alkali metal hydrogencarbonate; or alkaline earth metal carbonate.

Process For Producing Compound [73] From Compound [70]

Compound [73] can be produced by reacting compound [70] with a compound of the formula:

R³⁴—Z²H  [80]

wherein Z² and R³⁴ are as defined above, usually in the presence of a catalytic amount to an excess of an acid such as p-toluenesulfonic acid, hydrochloric acid or sulfuric acid, in an organic solvent such as benzene or chloroform.

The reaction temperature is in the range of −30° C. to the boiling temperature of the reaction mixture. The reaction time is in the range of a moment to 72 hours.

(Production Process 17)

This is the production process according to the following scheme:

wherein Q¹ and R¹ are as defined above.

Compound [82] can be produced by reacting compound [81] with a compound of the formula:

wherein R¹⁹ and R²² are as defined above, in a solvent.

The reaction temperature is usually in the range of 30° to 120° C., preferably 40° to 80° C. The reaction time is usually in the range of 5 to 72 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of compound [83] to 1 mole of compound [81] is ideal, can be changed depending upon the reaction conditions.

Examples the solvent which can be used include tertiary amines such as triethylamine.

After completion of the reaction, the reaction solvent is distilled out from the reaction mixture and the residue is subjected to chromatography, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired compound of the present invention can be isolated.

(Production Process 18)

This is the production process according to the following scheme:

wherein B³ is OR³⁵, SR³⁵, COOR³⁵, COR¹⁶, or CR¹⁷═CR¹⁸COR¹⁶ (wherein R³⁵ is (C₁-C₆ alkyl)carbonyl C₁-C₆ alkyl (C₁-C₆ haloalkyl)carbonyl C₁-C₆ alkyl, {(C₁-C₄ alkoxy) C₁-C₄ alkyl}carbonyl C₁-C₆ alkyl, or (C₃-C₈ cycloalkyl)carbonyl C₁-C₆ alkyl; and R¹⁶, R¹⁷, and R¹⁸ are as defined above); B⁴ is a substituent derived from B³ by protecting its ketone or aldehyde moiety with an alcohol; and X, Y, R¹, R², and R³ are as defined above.

Process For Producing Compound [100] From Compound [99]

Compound [100] can be produced in the same manner as described in Production Process 1, except that compound [99] is used in place of compound [4].

Process For Producing Compound [101] From Compound [100]

Compound [101] can be produced by deprotecting the ketal or acetal moiety of compound [100] by the ordinary method.

Compound [99] can be produced in the same manner as described below in the production process for compound [4], except that the ketone or aldehyde moiety in the substituent B³ of a compound of the formula:

wherein X, Y, and B³ are as defined above, is protected with an alcohol such as methanol to give a compound of the formula:

wherein X, Y, and B⁴ are as defined above, and compound [103] is used in place of compound [91] as described below.

Compound [5], which is one of the starting compounds in the production of the present compounds by production process 1, can be obtained from commercial sources or can be produced, for example, according to the method described in Jikken Kagaku Kouza (Maruzen K.K.), 4th ed., Vol. 24, pp. 259-260.

Compound [4], which is the other starting compound used in production process 1, can be produced by reacting a compound of the formula:

wherein R¹ and R³ are as defined above; and V is iodine, bromine, or chlorine, with water in the presence of a base to give a compound of the formula:

wherein R¹ and R³ are as defined above (hereinafter referred to as reaction 1), and then reacting compound [85] with a compound of the formula:

Q¹—NHNH₂  [86]

wherein Q¹ is as defined above (hereinafter referred to as reaction 2).

Compound [85] can also be reacted as its hydrate or acetal derivative in water or an alcohol.

Reaction 1 is usually effected in a solvent. The reaction temperature is usually in the range of 20° to 100° C. The reaction time is usually in the range of a moment to 24 hours. The amounts of the reagents to be used in the reaction, although the proportion of 2 moles of water and 2 moles of a base to 1 mole of compound [84] is ideal, can be changed, if necessary.

Examples of the base which can be used include organic bases and inorganic bases such as sodium acetate and potassium acetate.

Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitrites such as acetonitrile and isobutyronitrile; acid amides such as N,N-dimethylformamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; water; and mixtures thereof

Reaction 2 is usually effected in a solvent. The reaction temperature is usually in the range of −20° to 200° C. The reaction time is usually in the range of a moment to 72 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of compound [86] to 1 mole of compound [84] used in reaction 1 is ideal, can be freely changed depending upon the reaction conditions. If necessary, the hydrochloride salt or sulfate salt of compound [86] can also be used.

Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; fatty acids such as formic acid, acetic acid, and propionic acid; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; water; and mixtures thereof.

After completion of the reaction, the reaction mixture is filtered to collect the crystals, which may be precipitated by the addition of water, if necessary, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired product can be isolated.

Among the examples of compound [4], a compound of the formula:

wherein X is as defined above; Y² is halogen; and B² is hydrogen, halogen, C₁-C₆ alkoxy, or C₁-C₆ alkylthio, can also be produced according to the following scheme:

wherein X, Y², B², and R²² are as defined above.

Process For Producing Compound [89] From Compound [88]

Compound [89] can be produced by reacting compound [88] with a nitrite salt in hydrochloric acid or sulfuric acid to convert it into a diazonium salt, and then reacting the diazonium salt with a compound of the formula:

wherein R²² is as defined above, in the presence of a base such as sodium acetate or pyridine.

(see, e.g., Tetrahedron, Vol. 35, p. 2013 (1979))

Process For Producing Compound [90] From Compound [89]

Compound [90] can be produced by hydrolyzing compound [89] usually in the presence of a base in a solvent.

The reaction temperature is in the range of 0° to 150° C., preferably 20° to 100° C. The reaction time is in the range of 1 to 24 hours, preferably 1 to 10 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of a base to 1 mole of compound [89] is ideal, can be changed, if necessary.

Examples of the base which can be used include inorganic bases such as potassium hydroxide, lithium hydroxide, barium hydroxide, and sodium hydroxide.

Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chlorobenzene and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; nitro compounds such as nitromethane and nitrobenzene; acid amides such as N,N-dimethylformamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; water; and mixtures thereof.

Process For Producing Compound [87] From Compound [90]

Compound [87] can be produced by heating compound [90] in a solvent.

The reaction temperature is in the range of 50° to 200° C., preferably 50° to 150° C. The reaction time is in the range of a moment to 72 hours.

Examples of the solvent which can be used include aliphatic hydrocarbons such as hexane, heptane, ligroin, cyclohexane, and petroleum ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloromethane, dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and ethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitro compounds such as nitromethane and nitrobenzene; nitriles such as acetonitrile and isobutyronitrile; acid amides such as formamide, N,N-dimethylformamide, and acetamide; tertiary amines such as pyridine, triethylamine, diisopropylethylamine, N,N-dimethylaniline, N,N-diethylaniline, and N-methylmorpholine; sulfur compounds such as dimethylsulfoxide and sulforane; fatty acids such as formic acid, acetic acid, and propionic acid; alcohols such as methanol, ethanol, ethylene glycol, and isopropanol; water; and mixtures thereof.

The above reaction can also be effected with the use of a metal, e.g., copper, as a catalyst.

After completion of the reaction, the reaction mixture is filtered to collect the precipitated crystals, or the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired compound can be isolated.

Compound [86] can also be produced by the following scheme:

wherein Q¹ is as defined above.

(see Organic Synthesis Collective, Vol. 1, p.442)

Compound [91] is known in, or can be produced according to the method as described in, EP-61741-A; U.S. Pat. Nos. 4,670,046, 4,770,695, 4,709,049, 4,640,707, 4,720,297, 5,169,431; and JP-A63-156787/1988.

Some examples of compound [91] can also be produced according to the following scheme:

wherein R³¹ is COR¹⁶ or COOR¹⁰.

Process For Producing Compound [95] From Compound [94]

Compound [95] can be produced by reacting compound [94] with nitric acid in a solvent.

The reaction temperature is usually in the range of 0° to 100° C. The reaction time is usually in the range of a moment to 24 hours. The amounts of the reagents to be used in the reaction, although the proportion of 1 mole of nitric acid to 1 mole of compound [94] is ideal, can be freely changed depending upon the reaction conditions.

Examples of the solvent which can be used include acidic solvents such as mixtures of nitric acid and sulfuric acid.

(see Organic Synthesis Collective, Vol. 1, p. 372)

Process For Producing Compound [96] From Compound [95]

Compound [96] can be produced by reducing compound [95] in a mixture of acetic acid, iron powder, and water.

The reaction temperature is usually in the range of 0° to 100° C. The reaction time is usually in the range of a moment to 24 hours.

After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration, followed by, if necessary, subsequent purification by a technique such as column chromatography or recrystallization. Thus the desired compound can be isolated.

(see Organic Synthesis Collective, Vol. 2, p. 471, and ibid., Vol. 5, p. 829)

The present compounds have excellent herbicidal activity, and some of them exhibit excellent selectivity between crop plants and unfavorable weeds. In particular, the present compounds have herbicidal activity against various unfavorable weeds as recited below, which may cause trouble in the foliar treatment and soil treatment on upland fields.

Polygonaceae

wild buckwheat (Polygonum convolvulus), pale smartweed (Polygonum lapathifolium), Pennsylvania smartweed (Polygonum pensylvanicum), ladysthumb (Polygonum persicaria), curly dock (Rumex crispus), broadleaf dock (Rumex obtusifolius), Japanese knotweed (Polygonum cuspidatum)

Portulacaceae

common purslane (Portulaca oleracea)

Caryophyllaceae

common chickweed (Stellaria media)

Chenopodiaceae

common lambsquarters (Chenopodium album), kochia (Kochia scoparia)

Amaranthaceae

redroot pigweed (Amaranthus retroflexus), smooth pigweed (Amaranthus hybridus)

Crusiferae

wild radish (Raphaiius raphanistrum), wild mustard (Sinapis arvensis), shepherdspurse (Capsella bursa-pastoris)

Leguminosae

hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia), Florida beggarweed (Desmodium tortuosum), white clover (Trifolium repens)

Malvaceae

velvetleaf (Abutilon thieophrasti), prickly sida (Sida spinosa)

Violaceae

field pansy (Viola arvensis), wild pansy (Viola tricolor)

Rubiaceae

catchweed bedstraw (cleavers) (Galium aparine)

Convolvulaceae

ivyleaf morningglory (Ipomoea hederacea), tall morningglory (Ipomoea purpurea), entireleaf morningglory (Ipomoea hederacea var. integriuscula), pitted morningglory (Ipomoea lacunosa), field bindweed (Convolvulus arvensis)

Labiatae

red deadnettle (Lamium purpureum), henbit (Lamium amplexicaule)

Solanaceae

jimsonweed (Datura stramonium), black nightshade (Solanum nigrum)

Scrophulariaceae

birdseye speedwell (Veronica persica), ivyleaf speedwell (Veronica hederaefolia)

Compositae

common cocklebur (Xanthium pensylvanicum), common sunflower (Helianthus annuus), scentless chamomile (Matricaria perforata or inodora), corn marigold (Chrysanthemum segetum), pineappleweed (Matricaria matricarioides), common ragweed (Ambrosia artemisiifolia), giant ragweed (Ambrosia trifida), horseweed (Erigeron canadensis), Japanese mugwort (Artemisia princeps), tall goldenrod (Solidago altissima)

Boraginaceae

field forget-me-not (Myosotis arvensis)

Asclepiadaceae

common milkweed (Asclepias syriaca)

Euphorbiaceae

sun spurge (Euphorbia helioscopia), spotted spurge (Euphorbia maculata)

Gramnineae

barnyardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis), giant foxtail (Setaria faberi), large crabgrass (Digitaria sanguinalis), goosegrass (Eleusine indica), annual bluegrass (Poa annua), blackgrass (Alopecurus myosuroides), wild oat (Avena fatua), johnsongrass (Sorghum halepense), quackgrass (Agropyron repens), downy brome (Bromus tectorum), bermudagrass (Cynodon dactylon), fall panicum (Panicum dichotomiflorum), Texas panicum (Panicum texanum), shattercane (Sorghum vulgare)

Commelinaceae

common dayflower (Commelina communis)

Equisetaceae

field horsetail (Equisetum arvense)

Cyperaceae

rice flatsedge (Cyperus iria), purple nutsedge (Cyperus rotundus), yellow nutsedge (Cyperus esculentus)

Furthermore, some of the present compounds have no problematic phytotoxicity on main crops such as corn (Zea mays), wheat (Triticum aestivum), barley (Hordeum vulgare), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), cotton (Gossypium spp.), sugar beet (Beta vulgaris), peanut (Arachis hypogaea), sunflower (Helianthus annuus) and canoia (Brassica napus); garden crops such as flowers and ornamental plants; and vegetable crops.

The present compounds can attain effective control of unfavorable weeds in the no-tillage cultivation of soybean (Glycine max), corn (Zea mays), and wheat (Triticum aestivum). Furthermore, some of them exhibit no problematic phytotoxicity on crop plants.

The present compounds have herbicidal activity against various unfavorable weeds as recited below under the flooding treatment on paddy fields.

Gramineae

barnyardgrass (Echinochloa oryzicola)

Scrophulariaceae

common falsepimpernel (Lindernia procumbens)

Lythraceae

Rotala indica, Ammannia multiflora

Elatinaceae

Elatine triandra

Cyperaceae

smallflower umbrellaplant (Cyperus difformis), hardstem bulrush (Scirpus juncoides), needle spikerush (Eleocharis acicularis), Cyperus serotinus, Eleocharis kuroguwai

Pontederiaceae

Monochoria vaginalis

Alismataceae

Sagittaria pygmaea, Sagittaria trifolia, Alisma canaliculatum

Potamogetonaceae

roundleaf pondweed (Potamogeton distinctus)

Umbelliferae

Oenanthe javanica

Furthermore, some of the present compounds have no problematic phytotoxicity on transplanted paddy rice.

The present compounds can attain effective control of various unfavorable weeds in orchards, grasslands, lawns, forests, waterways, canals, or other non-cultivated lands.

The present compounds also have herbicidal activity against various aquatic plants such as water hyacinth (Eichhornia crassipes), which will grow in waterways, canals, or the like.

The present compounds have substantially the same characteristics as those of the herbicidal compounds described in the publication of International Patent Application, WO95/34659. In the case where crop plants with tolerance imparted by introducing a herbicide tolerance gene described in the publication are cultivated, the present compounds can be used at greater doses than those used when ordinary crop plants without tolerance are cultivated, and it is, therefore, possible to attain effective control of other unfavorable plants.

When the present compounds are used as active ingredients of herbicides, they are usually mixed with solid or liquid carriers or diluents, surfactants, and other auxiliary agents to give formulations such as emulsifiable concentrates, wettable powders, flowables, granules, concentrated emulsions, and water-dispersible granules.

These formulations may contain any of the present compounds as an active ingredient at an amount of 0.001% to 80% by weight, preferably 0.005% to 70% by weight, based on the total weight of the formulation.

Examples of the solid carrier or diluent may include fine powders or granules of the following materials: mineral matters such as kaolin clay, attapulgite clay, bentonite, terra alba, pyrophyllite, talc, diatomaceous earth, and calcite; organic substances such as walnut shell powder; water-soluble organic substances such as urea; inorganic salts such as ammonium sulfate; and synthetic hydrated silicon oxide. Examples of the liquid carrier or diluent may include aromatic hydrocarbons such as methylnaphthalene, phenylxylylethane, and alkylbenzenes (e.g., xylene); alcohols such as isopropanol, ethylene glycol, and 2-ethoxyethanol; esters such as phthalic acid dialkyl esters; ketones such as acetone, cyclohexanone, and isophorone; mineral oils such as machine oil; vegetable oils such as soybean oil and cotton seed oil; dimethylsulfoxide, N,N-dimethylformamide, acetonitrile, N-methylpyrrolidone, water, and the like.

Examples of the surfactant used for emulsification, dispersing, or spreading may include surfactants of the anionic type, such as alkylsulfates, alkylsulfonates, alkylarylsulfonates, dialkylsulfosuccinates, and phosphates of polyoxyethylene alkyl aryl ethers; and surfactants of the nonionic type, such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters.

Examples of the auxiliary agent used for formulation may include ligninsulfonates, alginates, polyvinyl alcohol, gum arabic, carboxymethyl cellulose (CMC), and isopropyl acid phosphate (PAP).

The present compounds are usually formulated as described above and then used for the pre- or post-emergence soil, foliar, or flooding treatment of unfavorable weeds. The soil treatment may include soil surface treatment and soil incorporation. The foliar treatment may include application over the plants and directed application in which a chemical is applied only to the unfavorable weeds so as to keep off the crop plants.

The present compounds can be used, if necessary, in combination with other compounds having herbicidal activity. Examples of the compounds which can be used in combination with the present compounds may include various compounds described in Catalog 1995 Edition of Farm Chemicals Handbook (Meister Publishing Company); AG CHEM NEW COMPOUND REVIEW, VOL. 13, 1995 (AG CHEM INFORMATION SERVICE); or JOSOUZAI KENKYU SOURAN (Hakuyu-sha). Typical examples of such compounds are as follows: atrazin, cyanazine, dimethametryn, metribuzin, prometryn, simazine, simetryn, chlorotoluron, diuron, dymuron, fluometuron, isoproturon, linuron, methabenzthiazuron, bromoxynil, ioxynil, ethalfluralin, pendimethalin, trifluralin, acifluorfen, acifluorfen-sodium, bifenox, chlomethoxynil, fomesafen, lactofen, oxadiazon, oxyfluorfen, carfentrazone, flumiclorac-pentyl, flumioxazine, fluthiacet-methyl, sulfentrazone, thidiazimin, difenzoquat, diquat, paraquat, 2,4-D, 2,4-DB, DCPA, MCPA, MCPB, clomeprop, clopyralid, dicamba, dithiopyr, fluroxypyr, mecoprop, naploanilide, phenothiol, quinclorac, triclopyr, acetochlor, alachlor, butachlor, diethatylethyl, metolachlor, pretilachlor, propachlor, bensulfuron-methyl, chlorsulfuron, chlorimuron-ethyl, halosulfuron-methyl, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, sulfometuron-methyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, azimsulfuron, cloransulam-methyl, cyclosulfamuron, flumeturam, flupyrsulfuron, flazasulfuron, imazosulfuron, metosulam, prosulfuron, rimsulfuron, triflusulfuron-methyl, imazamethabenz-methyl, imazapyr, imazaquin, imazethapyr, imazameth, imazamox, bispyribac-sodium, pyriminobac-methyl, pyrithiobac-sodium, alloxydimsodium, clethodim, sethoxydim, tralkoxydim, diclofop-methyl, fenoxaprop-ethyl, fenoxaprop-p-ethyl, fluazifop-butyl, fluazifop-p-butyl, haloxyfop-methyl, quizalofop-p-ethyl, cyhalofop-butyl, clodinafop-propargyl, benzofenap, clomazone, diflufenican, norflurazon, pyrazolate, pyrazoxyfen, isoxaflutole, sulcotrione, glufosinate-ammonium, glyphosate, bentazon, benthiocarb, bromobutide, butamifos, butylate, dimepiperate, dimethenamid, DSMA, EPTC, esprocarb, isoxaben, mefenacet, molinate, MSMA, piperophos, pributycarb, propanil, pyridate, triallate, cafenstrol, flupoxam, and thiafluamide.

The following will describe typical examples of such a combination, where the present compounds are designated by their compound numbers shown in Tables 1 to 5.

1. A mixture of one compound selected from the group consisting of compounds 1-495, 1-496, 1-499, 1-503 and 1-577, and one compound selected from the group consisting of atrazin, cyanazine, bromoxynil and bentazon at a weight ratio of 1:1 to 100.

2. A mixture of one compound selected from the group consisting of compounds 1-495, 1-496, 1-499, 1-503 and 1-577, and one compound selected from the group consisting of clethodim, sethoxydim, dichbofop-methyl, quizalofop-p-ethyl, lactofen, acifluorfen, acifluorfen-sodium, fomesafen, flurniclorac-pentyl and dicamba at a weight ratio of 1:0.5 to 50.

3. A mixture of one compound selected from the group consisting of compounds 1-495, 1-496, 1-499, 1-503 and 1-577, and one compound selected from the group consisting of nicosulfuron, primisulfuron, prosulfuron, chlorimuran-ethyl, thifensulfuron, rimsulfuron, halosulfuron, oxasulfuron, isoxaflutole, imazethapyr and imazamox at a weight ratio of 1:0.1 to 10.

4. A mixture of one compound selected from the group consisting of compounds 1-439, 1-482, 1-486, 1-496, 1-1076, 1-1123 and 1-1441, and one compound selected from the group consisting of isoproturon and chlorotoluron at a weight ratio of 1:1 to 100.

5. A mixture of one compound selected from the group consisting of compounds 1-439, 1-482, 1-486, 1-496, 1-1076, 1-1123 and 1-1441, and one compound selected from the group consisting of mecoprop, fluroxypyr and ioxynil at a weight ratio of 1:0.5 to 50.

6. A mixture of one compound selected from the group consisting of compounds 1-439, 1-482, 1-486, 1-496, 1-1076, 1-1123 and 1-1441, and one compound selected from the group consisting of diflufenican, metsulfuron-methyl, fenoxaprop-ethyl and clodinafop-propargyl at a weight ratio of 1:0.1 to 10.

7. A mixture of one compound selected from the group consisting of compounds 1-1141, 1-1222 and 2-203, and one compound selected from the group consisting of glyphosate, glufosinate-ammonium and paraquat at a weight ratio of 1:1 to 100.

Moreover, the present compounds may also be used in admixture with insecticides, acaricides, nematocides, fungicides, plant growth regulators, fertilizers, soil improver, and the like.

When the present compounds are used as active ingredients of herbicides, the application amount is usually in the range of 0.01 to 10,000 g, preferably 1 to 8000 g, per hectare, although it may vary depending upon the weather conditions, formulation type, application timing, application method, soil conditions, crop plants, unfavorable weeds, and the like. In the case of emulsifiable concentrates, wettable powders, flowables, concentrated emulsions, water-dispersible granules, or the like, the formulation is usually applied at a prescribed amount after diluted with water having a volume of about 10 to 1000 liters per hectare, if necessary, with the addition of an adjuvant such as a spreading agent. In the case of granules or some types of flowables, the formulation is usually applied as such without any dilution.

Examples of the adjuvant used, if necessary, may include, in addition to the surfactants recited above, polyoxyethylene resin acids (esters), ligninsulfonates, abietates, dinaphthylmethanedisulfonates, crop oil concentrates, and vegetable oils such as soybean oil, corn oil, cotton seed oil, and sunflower oil.

The present compounds can also be used as active ingredients of harvesting aids such as defoliants and desiccating agents for cotton, and desiccating agents for potato. In these cases, the present compounds are usually formulated in the same manner as the case where they are used as active ingredients of herbicides, and used alone or in combination with other harvesting aids for foliar treatment before the harvesting of crops.

The present invention will be further illustrated by the following production examples, reference examples, formulation examples, and test examples; however, the present invention is not limited to these examples.

The following will describe production examples for the present compounds and the hydrazones of formula [2] as the intermediate compounds, where the present compounds are designated by their compound numbers shown in Tables 1 to 5.

PRODUCTION EXAMPLE 1

(Production of Compound 2-631)

To a mixed solution of 8.0 g (97.2 mmol) of sodium acetate and 50 ml of water was added under ice cooling 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed to proceed at 80° C. for 30 minutes. Then, the reaction mixture was cooled to 0° C., to which 4.4 g (18.7 mmol) of 7-fluoro-6-hydrazino-4-propargyl-2H-1,4-benzoxazin-3-one was added, and the reaction mixture was stirred at room temperature for 2 hours. The precipitated crystals were collected by filtration, washed twice with 10 ml of water, and dried, which afforded 6.3 g (18.37 mmol) of 7-fluoro-6-trifluoroacetylmethylidenhydrazino-4-propargyl-2H-1,4-benzoxazin-3-one [another name: 3,3,3-trifluoro-2-oxopropanal 1-(7-fluoro-3-oxo-4-propargyl-2H-1,4-benzoxazin-6-ylhydrazone)], m.p. 190.6° C. (decomp.).

To a mixed solution of 6.0 g (1 7.5 mmol) of the above compound and 50 ml of toluene was added 9.1 g (26.2 mmol) of carbethoxymethylenetriphenylphosphorane, and the mixture was heated under reflux for 1 hour. The toluene was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 1.3 g (3.5 mmol) of 7-fluoro-6-[5-trifluoromethyl-3-pyridazinon-2-yl]-4-propargyl-2H-1,4-benzoxazin-3-one (compound 2-631).

PRODUCTION EXAMPLE 2

(Production of Compound 1-476)

To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate and about 100 ml of water was added under ice cooling 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed to proceed at 70° C. for 20 minutes. Then, the reaction mixture was cooled to room temperature, to which a solution of 5.8 g (21.5 mmol) of 2-fluoro-4-chloro-5-isopropoxyphenylhydrazine dissolved in about 20 ml of diethyl ether was added, and the reaction mixture was stirred at room temperature for 1 hour. The ether layer was separated and concentrated. Then, about 60 ml of THF was added to the residue, to which 8.3 g (23.0 mmol) of carbethoxyethylidenetriphenylphosphorane was added, and the mixture was heated under reflux for 2 hours. The toluene was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 3.8 g (10.5 mmol) of 2-[2-fluoro-4-chloro-5-isopropoxyphenyl]-4-methyl-5-trifluoromethylpyridazin-3-one (compound 1-476).

PRODUCTION EXAMPLE 3

(Production of Compound 1-391)

First, 3.5 g (9.7 mmol) of 2-[2-fluoro-4-chloro-5-isopropoxyphenyl]-4-methyl-5-trifluoromethylpyridazin-3-one (compound 1-476) was dissolved in about 10 ml of concentrated sulfuric acid under ice cooling, and the solution was warmed to room temperature. After 10 minutes, about 100 ml of water was added to the reaction mixture, and the precipitated crystals were collected by filtration, and washed twice with 20 ml of water and once with 10 ml of hexane. These crystals were recrystallized from isopropanol, which afforded 3.2 g (9.0 mmol) of 2-[2-fluoro-4-chloro-5-hydroxy-phenyl]-4-methyl-5-trifluoromethylpyridazin-3-one (compound 1-391).

PRODUCTION EXAMPLE 4

(Production of Compound 1-486)

First, 3.2 g (10 mmol) of compound 1-391 was dissolved in about 50 ml of DMF, to which 2.0 g (13 mmol) of potassium carbonate was added at room temperature and 1.3 g (11 mmol) of propargyl bromide was then added, and the mixture was stirred at room temperature for 30 minutes, followed by the addition of 100 ml of water. The precipitated crystals were collected by filtration, washed with hexane, and recrystallized from isopropanol, which afforded 3.4 g (9 mmol) of compound 1-486.

PRODUCTION EXAMPLE 5

(Production of Compound 1-496)

First, 3.2 g (10 mmol) of compound 1-391 was dissolved in about 50 ml of DMF, to which 0.44 g (11 mmol) of sodium hydride (60 wt. %, oil dispersion) was added, and the mixture was allowed to stand at room temperature for 30 minutes, followed by the addition of 1.8 g (11 mmol) of ethyl bromoacetate under ice cooling. After stirring at room temperature for 1 hour, the reaction mixture was extracted with diethyl ether. The organic layer was washed with 10% aqueous HCl, aqueous sodium bicarbonate solution and then with saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 2.4 g (5.5 mmol) of compound 1-496.

PRODUCTION EXAMPLE 6

(Production of Compound 2-25 1)

To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate and about 50 ml of water was added under ice cooling 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed to proceed at 80° C. for 1 hour. Then, the reaction mixture was cooled to 0° C., to which 4.4 g (18.7 mmol) of 7-fluoro-6-hydrazino-4-propargyl-2H-1,4-benzoxazin-3-one was added, and the reaction mixture was stirred at room temperature for 2 hours. The precipitated crystals were collected by filtration, washed twice with 10 ml of water and once with 10 ml of hexane, and then dissolved in 50 ml of toluene without drying. To this solution was added 8.8 g (24.3 mmol) of carbethoxyethylidenetriphenylphosphorane, and the mixture was heated under reflux for 1 hour, while conducting azeotropic dehydration. The toluene was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 3.5 g (9.01 mmol) of compound 2-251.

PRODUCTION EXAMPLE 7

(Production of Compound 2-328)

To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate and about 50 ml of water was added under ice cooling 6.6 g (24.3 mmol) of 1,I-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed to proceed at 80° C. for 1 hour. Then, the reaction mixture was cooled to 0° C., to which 4.8 g (18.7 mmol) of 6-fluoro-5-hydrazino-3-(sec-butyl)-1,3-benzothiazol-2-one was added, and the reaction mixture was stirred at room temperature for 2 hours. Then, 100 ml of ether was added to the reaction mixture, followed by stirring and phase separation, and the organic layer was concentrated. The residue was dissolved in 50 ml of THF, to which 8.8 g (24.3 mmol) of carbethoxyethylidenetriphenylphosphorane was added, and the mixture was heated under reflux for 1 hour. The THF was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 3.7 g (9.6 mmol) of compound 2-328.

PRODUCTION EXAMPLE 8

(Production of Compound 1-347)

First, 50 ml of concentrated sulfuric acid was ice cooled, in which 7.0 g (22.8 mmol) of compound 1-341 was dissolved. Then, 1.51 g (24 mmol) of fuming nitric acid was added dropwise at 5° C. or lower, followed by maturation at 0° to 5° C. for 1 hour. The mixture was poured into 300 ml of ice-water and extracted three times with 50 ml of ether. The combined ether layer was washed with about 100 ml of water and neutralized with 100 ml of aqueous sodium bicarbonate solution, followed by phase separation. The organic layer was dried with magnesium sulfate and concentrated to half volume, and the residue was subjected to silica gel column chromatography, which afforded 6.1 g (17.4 mmol) of compound 1-347.

PRODUCTION EXAMPLE 9

(Production of Compound 1-353)

First, 5.0 g of iron powder, 75 ml of acetic acid, and 10 ml of water were mixed, and the mixture was warmed to about 80° C., followed by maturation for about 15 minutes. Then, 6.0 g (17.1 mmol) of compound 1-347 was dissolved in 40 ml of ethyl acetate, which was added dropwise to the above mixture at 80° C. or lower. After maturation at about 80° C. for 1 hour, the reaction mixture was allowed to stand for cooling to room temperature, and extracted twice with 100 ml of ethyl acetate. The combined ethyl acetate layer was washed twice with 50 ml of water and neutralized with aqueous sodium bicarbonate solution, followed by phase separation. The organic layer was dried with magnesium sulfate, and the ethyl acetate was distilled out under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 5.1 g (15.9 mmol) of compound 1-353.

PRODUCTION EXAMPLE 10

(Production of Compound 1-420)

First, 500 mg (1.6 mmol) of compound 1-353 was mixed with 10 ml (77.3 mmol) of ethyl 2-bromopropionate, and the mixture was heated under reflux at about 160° C. for about 12 hours. After allowing to stand for cooling, the reaction mixture was subjected to silica gel column chromatography, which afforded 60 mg (0.6 mmol) of compound 1-420.

PRODUCTION EXAMPLE 11

(Production of Compound 1-1622)

First, 6 ml (55.4 mmol) of ethyl acrylate, 0.5 g (4.8 mmol) of t-butyl nitrite, and 0.6 g (4.5 mmol) of copper (II) chloride were mixed together in 5 ml of acetonitrile, followed by ice cooling. Then, 1.0 g (3.1 mmol) of compound 1-353 dissolved in 5 ml of acetonitrile was added dropwise at 5° C. or lower, followed by overnight maturation at room temperature. The reaction mixture was poured into ice-water and extracted twice with 100 ml of ethyl acetate. The combined ethyl acetate layer was washed with 50 ml of diluted hydrochloric acid and dried with magnesium sulfate. The solvent was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 0.51 g (1.2 mmol) of compound 1-1622.

PRODUCTION EXAMPLE 12

(Production of Compound 1-1221)

To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate and about 50 ml of water was added under ice cooling 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed to proceed at 80° C. for 1 hour. Then, the reaction mixture was cooled to 0° C., to which 5.2 g (18.7 mmol) of methyl 2-(2-chloro-4-fluoro-5-hydrazinophenylthio)propionate was added, and the reaction mixture was stirred at room temperature for 2 hours. The precipitated crystals were collected by filtration, washed twice with 10 ml of water and once with 10 ml of hexane, and dried. The residue was dissolved in 50 ml of THF, to which 8.4 g (22.4 mmol) of carbethoxymethylenetriphenylphosphorane was added, and the solution was stirred at room temperature for 3 hours. The THF was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 3.8 g (9.0 mmol) of compound 1-1221.

PRODUCTION EXAMPLE 13

(Production of Compound 2-821)

To a mixed solution of 8.0 g (97.2 mmol) of sodium acetate and about 50 ml of water was added under ice cooling 6.9 g (24.3 mmol) of 3,3-dibromo-1,1,1-trifluorobutanone, and the reaction was allowed to proceed at 80° C. for 30 minutes. Then, the reaction mixture was cooled to 0° C., to which 4.4 g (18.7 mmol) of 7-fluoro-6-hydrazino-4-propargyl-2H-1,4-benzoxazin-3-one was added, and the reaction mixture was stirred at room temperature for 2 hours. The precipitated crystals were collected by filtration, washed twice with 10 ml of water, and dried, which afforded 6.1 g (17.0 mmol) of 1,1,1-trifluoro-2,3-butandione 3-(7-fluoro-3-oxo-4-propargyl-2H-1,4-benzoxazin-6-ylhydrazone).

To a mixed solution of 6.1 g (17.0 mmol) of the above compound and 50 ml of THF was added 7.1 g (20.4 mmol) of carbethoxymethylenetriphenylphosphorane, and the mixture was heated under reflux for 1 hour. The THF was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 0.61 g (1.6 mmol) of 7-fluoro-6-(6-methyl-5-trifluoromethyl-3-pyridazinon-2-yl)-4-propargyl-2H-1,4-benzoxazin-3-one (compound 2-821).

Reference Example 1

This is a production example for 3,3-dibromo-1,1,1-trifluoro-2-butanone used in Production Example 13.

First, 34.0 g of sodium acetate was dissolved in 270 ml of acetic acid, to which 25 g (0.20 mol) of 1,1,1-trifluoro-2-butanone was added, and while keeping the temperature at 15° to 20° C., 66.3 g (0.42 mol) of bromine was added dropwise over 45 minutes. The reaction mixture was stirred for 5 hours, while keeping the temperature at 15° to 20° C., and then allowed to stand at room temperature for 68 hours. The supernatant was taken and washed with 600 ml of concentrated sulfuric acid. Further washing with 307 ml of concentrated sulfuric acid and distillation under normal pressure gave 28 g (0.10 mol) of 3,3-dibromo-1,1,1-trifluoro-2-butanone.

PRODUCTION EXAMPLE 14

(Production of Compound 1-1346)

To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate and about 50 ml of water was added under ice cooling 6.9 g (24.3 mmol) of 3,3-dibromo-1,1,1-trifluoro-2-butanone, and the reaction was allowed to proceed at 80° C. for 1 hour. Then, the reaction mixture was cooled to 0° C., to which 3.3 g (18.7 mmol) of 2-chloro-4-fluoro-5-hydrazinophenol was added, and the reaction mixture was stirred at room temperature for 2 hours. The precipitated crystals were collected by filtration, washed twice with 10 ml of water and once with 10 ml of hexane, dried, and then dissolved in 50 ml of THF. To this solution was added 8.8 g (24.3 mmol) of carbethoxymethylenetriphenylphosphorane, and the mixture was stirred at room temperature for 3 hours. The THF was distilled out under reduced pressure, and the residue was subjected to silica gel chromatography, which afforded 0.51 g (1.6 mmol) of compound 1-1346.

PRODUCTION EXAMPLE 15

(Production of Compound 1-1441)

First, 3.2 g (10 mmol) of compound 1-1346 was dissolved in about 50 ml of DMF, to which 2.0 g (13 mmol) of potassium carbonate was added at room temperature and 1.3 g (11 mmol) of propargyl bromide was then added, and the mixture was stirred at room temperature for 30 minutes, followed by the addition of 100 ml of water. The precipitated crystals were collected by filtration, washed with hexane, and recrystallized from isopropanol, which afforded 3.2 g (8.5 mmol) of compound 1-1441.

PRODUCTION EXAMPLE 16

(Production of Compound 1-499)

This example followed the procedures of Production Example 5, except that 1.8 g (1.1 mmol) of n-pentyl chloroacetate was used in place of ethyl bromoacetate. After the addition of this compound, the reaction mixture was stirred at 40° C. for 3 hours and then extracted with diethyl ether. The organic layer was washed with 10% HCl, aqueous sodium bicarbonate solution and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure, and the residue was subjected to silica gel chromatography, which afforded 3.8 g (8.0 mmol) of compound 1-499.

PRODUCTION EXAMPLE 17

(Production of Compound 2-203)

To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate and about 50 ml of water was added under ice cooling 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed to proceed at 80° C. for 1 hour. Then, the reaction mixture was cooled to 0° C., to which 4.0 g (1 8.7 mmol) of 6-hydrazino-4-propargyl-2H-1,4-benzoxazin-3-one was added, and the reaction mixture was stirred at room temperature for 2 hours. The precipitated crystals were collected by filtration, washed twice with 10 ml of water and once with 10 ml of hexane, and then dissolved in 50 ml of THF without drying. To this solution was added 8.8 g (24.3 mmol) of carbethoxyethylidenetriphenylphosphorane, and the mixture was heated under reflux for 3 hours. The THF was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 3.3 g (8.8 mmol) of compound 2-203.

PRODUCTION EXAMPLE 18

(Production of Compound 1-1222)

To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate and about 50 ml of water was added under ice cooling 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed to proceed at 80° C. for 1 hour. Then, the reaction mixture was cooled to 0° C., to which 5.5 g (18.7 mmol) of ethyl 2-(2-chloro-4-fluoro-5-hydrazinophenylthio)propionate was added, and the reaction mixture was stirred at room temperature for 2 hours. The precipitated crystals were collected by filtration, washed twice with 10 ml of water and once with 10 ml of hexane, dried, and then dissolved in 50 ml of THF. To this solution was added 8.4 g (22.4 mmol) of carbethoxymethylenetriphenylphosphorane, and the mixture was stirred at room temperature for 3 hours. The THF was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 4.3 g (9.9 mmol) of compound 1-1222.

PRODUCTION EXAMPLE 19

(Production of Compound 1-476)

To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate and about 100 ml of water was added under ice cooling 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed to proceed at 70° C. for 20 minutes. Then, the reaction mixture was cooled to room temperature, to which a solution of 5.8 g (21.5 mmol) of 2-fluoro-4-chloro-5-isopropoxyphenylhydrazine dissolved in about 20 ml of diethyl ether was added, and the reaction mixture was stirred at room temperature for 1 hour. The ether layer was separated, washed once with 10 ml of saturated sodium chloride solution, and dried with magnesium sulfate. The diethyl ether was distilled out, which afforded 6.5 g (20.0 mmol) of 3,3,3-trifluoro-2-oxo-propanal 1-(4-chloro-2-fluoro-5-isopropoxyphenylhydrazone).

¹H-NMR (250 MHz, CDCl₃, TMS δ (ppm)) 1.39 (6H, d, J=6.0 Hz), 4.38-4.52 (1H, m), 7.15 (1H, d, J=10.5 Hz), 7.22 (1H, d, J=7.3 Hz), 7.43 (1H, q, J=1.7 Hz), 9.18 (1H, br).

This compound was dissolved in 50 ml of THF. To this solution was added 8.3 g (23.0 mmol) of carbethoxyethylidenetriphenylphosphorane, and the mixture was heated under reflux for 2 hours. The THF was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 3.8 g (10.5 mmol) of 2-[2-fluoro-4-chloro-5-isopropoxyphenyl]-4-methyl-5-trifluoromethylpyridazin-3-one (compound 1-476).

PRODUCTION EXAMPLE 20

(Production of Compound 1-642)

To a mixed aqueous solution of 5.3 g (53.5 mmol) of sodium acetate and about 100 ml of water was added under ice cooling 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed to proceed at 70° C. for 20 minutes. Then, the reaction mixture was cooled to room temperature. Separately, 5.8 g (21.5 mmol) of crude ethyl 2-chloro-4-fluoro-5-hydrazinobenzoate hydrochloride was dissolved in 30 ml of water, to which 100 ml of diethyl ether was added, and while cooling, the mixture was neutralized by the addition of saturated sodium hydrogencarbonate solution, followed by washing with saturated sodium chloride solution, which afforded a solution of ethyl 2-chloro-4-fluoro-5-hydrazinobenzoate in diethyl ether. This solution was added to the above reaction mixture, followed by vigorous stirring at room temperature for 2 hours. The ether layer was separated, washed once with 10 ml of saturated sodium chloride solution, and dried with magnesium sulfate. The diethyl ether was distilled out. The residue was dissolved in 50 ml of THF, to which 8.3 g (23.0 mmol) of carbethoxyethylidenetriphenylphosphorane was added, and the mixture was heated under reflux for 2 hours. The THF was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 3.8 g (10.0 mmol) of compound 1-642.

Reference Example 2

This is a production example for ethyl 2-chloro-4-fluoro-5-hydrazinobenzoate hydrochloride used in Production Example 20.

First, 50 g (0.29 mol) of 2-chloro-4-fluorobenzoic acid was dissolved in 150 ml of hydrochloric acid at room temperature, to which a mixed acid of 28 ml (0.31 mol) of fuming nitric acid and 56 ml of concentrated sulfuric acid was added dropwise at 35° to 45° C. Then, the solution was stirred at 40° C. for 1 hour and poured into 250 ml of ice-water. The precipitated crystals were collected by filtration and recrystallized from a mixed solution of hexane and ethyl acetate, which afforded 55 g (0.25 mol) of 2-chloro-4-fluoro-5-nitrobenzoic acid. Then, 55 g (0.25 mol) of 2-chloro-4-fluoro-5-nitrobenzoic acid was dissolved in 50 ml of ethyl acetate, to which 33 g (0.28 mol) of thionyl chloride was added, and the mixture was heated under reflux for 3 hours and then allowed to stand for cooling to room temperature. Then, 20 ml of ethanol and 30 g of triethylamine were added under ice cooling, and the mixture was stirred at room temperature for 2 hours. The solvent was distilled out, and the residue was purified by silica gel chromatography, which afforded 57 g (0.23 mol) of ethyl 2-chloro-4-fluoro-5-nitrobenzoate.

Then, 60 g of iron powder and 500 ml of 10% acetic acid were mixed, and the mixture was heated to 40° C. Separately, 50 g (0.20 mol) of ethyl 2-chloro-4-fluoro-5-nitrobenzoate was dissolved in a mixed solution of 20 ml of acetic acid and 20 ml of ethyl acetate, and added dropwise to the above iron powder-acetic acid mixed solution. Then, the reaction mixture was stirred at 50° C. for 1 hour and filtered though celite. The filtrate was extracted with 100 ml of ethyl acetate. The ethyl acetate layer was washed with aqueous sodium bicarbonate solution and saturated sodium chloride solution, and dried with magnesium sulfate. The solvent was distilled out, and the residue was purified by silica gel chromatography, which afforded to 40 g (0.18 mol) of ethyl 5-amino-2-chloro-4-fluorobenzoate.

Then, 19 g (87.4 mmol) of ethyl 5-amino-2-chloro-4-fluorobenzoate was dissolved in 120 ml of hydrochloric acid, followed by cooling to 0° C., to which a solution of 6.3 g (91.7 mmol) of sodium nitrite dissolved in 10 ml of water was added dropwise at 10° C. or lower. The mixture was stirred at 0° C. for 30 minutes and then cooled to −30° C., into which a solution of 58 g (0.31 mol) of anhydrous tin (II) chloride dissolved in 40 ml of hydrochloric acid was poured, followed by further stirring at 0° C. for 3 hours. The precipitated crystals were collected by filtration and then dried, which afforded 13.6 g (50.7 mmol) of crude ethyl 2-chloro-4-fluoro-5-hydrazinobenzoate hydrochloride.

PRODUCTION EXAMPLE 21

(Production of Compound 1-1789)

First, 5.0 g (15.5 mmol) of compound 1-391 was dissolved in about 50 ml of DMF, to which 2.8 g (20.2 mmol) of potassium carbonate was added at room temperature and then 1.5 g (17.1 mmol) of 3-bromo-2-methyl-1-propene was added, and the mixture was stirred at room temperature for 30 minutes, followed by the addition of 100 ml of water. The precipitated crystals were collected by filtration, washed with hexane, and recrystallized from isopropanol, which afforded 4.4 g (13.2 mmol) of compound 1-1789.

PRODUCTION EXAMPLE 22

(Production of Compound 4-45 1)

First, 4.0 g (12.0 mmol) of compound 1-1789 was dissolved in 20 ml of N,N-dimethylaniline, and the solution was heated at 180° C. for 3 hours. After cooling to room temperature, 100 ml of ethyl acetate was added, and the mixture was washed with 1N aqueous hydrochloric acid and saturated sodium chloride solution, and dried with magnesium sulfate. The solvent was distilled out, and the precipitated crystals were recrystallized from isopropanol, which afforded 3.4 g (10.2 mmol) of 2-[4-chloro-6-fluoro-3-hydroxy-2-(2-methyl-2-propenyl)]-4-methyl-5-trifluoromethylpyridazin-3-one, m.p. 133.2° C.

The product was dissolved in 30 ml of xylene, to which a catalytic amount of p-toluenesulfonic acid was added, and the mixture was heated under reflux for 1 hour. After cooling to room temperature, 100 ml of ethyl acetate was added, and the mixture was washed with aqueous sodium bicarbonate solution and sodium chloride solution, and dried with magnesium sulfate. The solvent was distilled out, and the residue was purified by silica gel column chromatography, which afforded 3.0 g (9.0 mmol) of compound 4-45 1.

PRODUCTION EXAMPLE 23

(Production of Compound 1-483)

First, 5.0 g (15.5 mmol) of compound 1-391 was dissolved in about 20 ml of DMF, to which 2.4 g (17.1 mmol) of potassium carbonate was added at room temperature. The solution was heated to about 40° C., to which 1.7 g (17.1 mmol) of 2,3-dichloropropene was added, and after 1 hour, the mixture was allowed to stand for cooling and poured into ice-water. The precipitated crystals were collected by filtration, washed with hexane, and recrystallized from isopropanol, which afforded 5.2 g (13.1 mmol) of compound 1-483.

PRODUCTION EXAMPLE 24

(Production of Compound 3-139)

First, 3.0 g (7.6 mmol) of compound 1-436 was dissolved in 10 ml of N,N-dimethylaniline, and the solution was heated under reflux for 3 hours. After cooling to room temperature, 50 ml of ethyl acetate was added, and the mixture was washed with 1N aqueous hydrochloric acid and saturated sodium chloride solution, and dried with magnesium sulfate. The solvent was distilled out, and the precipitated crystals were recrystallized from isopropanol, which afforded 2.2 g (5.6 mmol) of 2-[4-chloro-6-fluoro-3-hydroxy-2-(2-chloro-2-propenyl)]-4-methyl-5-trifluoromethylpyridazin-3-one.

¹H-NMR (300 MHz, CDCl₃, TMS δ (ppm)) 2.41 (3H, q, J=1.9 Hz), 3.56 (1H, d, J=16.3 Hz), 3.72 (1H, d, J=16.3 Hz), 4.91 (1H, q, J=1.4 Hz), 5.12 (1H, d, J=1.5 Hz), 5.72 (1H, s), 7.25 (1H, d, J=8.7 Hz), 8.00 (1H, s)

The product was dissolved in 10 ml of trifluoromethanesulfonic acid cooled by ice, and the solution was stirred under ice cooling. After 30 minutes, the solution was poured into ice-water, and the precipitated crystals were collected by filtration and subjected to silica gel column chromatography, which afforded 1.9 g (5.4 mmol) of compound 3-139.

PRODUCTION EXAMPLE 25

(Production of Compound 1-1744)

This example followed the procedures of Production Example 20, except that 6.1 g (21.5 mmol) of ethyl 2,4-dichloro-5-hydrazinobenzoate hydrochloride was used in place of ethyl 2-chloro-4-fluoro-5-hydrazinobenzoate hydrochloride, which afforded 4.8 g (12.2 mmol) of compound 1-1744.

The ethyl 2,4-dichloro-5-hydrazinobenzoate hydrochloride used above was produced from 2,4-dichlorobenzoic acid by the same process as shown in Reference Example 2.

PRODUCTION EXAMPLE 26

(Production of Compound 1-1279)

To a mixed aqueous solution of 5.3 g (53.5 mmol) of sodium acetate and about 100 ml of water was added under ice cooling 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed to proceed at 70° C. for 20 minutes. Then, the reaction mixture was cooled to room temperature. Separately, 5.8 g (21.5 mmol) of ethyl 2-chloro-4-fluoro-5-hydrazinobenzoate hydrochloride was dissolved in 30 ml of water, to which 100 ml of diethyl ether was added, and while cooling, the mixture was neutralized by the addition of saturated sodium hydrogencarbonate solution, followed by washing with saturated sodium chloride solution, which afforded a solution of ethyl 2-chloro-4-fluoro-5-hydrazinobenzoate in diethyl ether. This solution was added to the above reaction mixture, followed by vigorous stirring at room temperature for 2 hours. The ether layer was separated, washed once with 10 ml of saturated sodium chloride solution, and dried with magnesium sulfate. The diethyl ether was distilled out, and a small amount of hexane was added to give 4.3 g (12.6 mmol) of ethyl 2-chloro-4-fluoro-5-(2-oxo-3,3,3-trifluoropentylidenehydrazino)benzoate. This product was dissolved in 50 ml of THF, to which 5.0 g (14.4 mmol) of carbethoxymethylenetriphenylphosphorane was added, and the mixture was heated under reflux for 2 hours. The THF was distilled out under reduced pressure, and the residue was subjected to silica gel column chromatography, which afforded 3.6 g (9.7 mmol) of compound 1-1279.

PRODUCTION EXAMPLE 27

(Production of Compound 1-1780)

First, 50 g (0.61 mol) of sodium acetate and 41 g (0.14 mol) of 1,1-dibromo-3,3,3-trifluoroacetone were mixed with 500 ml of water, and the mixture was stirred at 80° C. for 30 minutes and then cooled to 0° C. Then, 45 g (0.14 mol) of 4-bromo-2-fluoro-5-isopropoxyphenylhydrazine hydrochloride was added at 10° C. or lower, and the mixture was stirred at 10° C. or lower for 3 hours. The precipitated crystals were collected by filtration and dried, which afforded 35 g (94.3 mmol) of 3,3,3-trifluoro-2-oxopropanal 1-(4-bromo-2-fluoro-5-isopropoxyphenylhydrazone).

Then, 16 g (46.0 mmol) of carbethoxymethylenetriphenylphosphorane and 16 g (43.1 mmol) of 3,3,3-trifluoro-2-oxopropanal 1-(4-bromo-2-fluoro-5-isopropoxyphenylhydrazone) were stirred in 100 ml of THF at room temperature for 4 hours. After completion of the reaction, the reaction mixture was concentrated, and the residue was subjected to silica gel chromatography, which afforded 9.4 g (23.8 mmol) of compound 1-1780.

Reference Example 3

This is a production example for 4-bromo-2-fluoro-5-isopropoxyphenylhydrazine hydrochloride used in Production Example 27.

First, 93 g (0.49 mol) of 2-bromo-4-fluorophenol was suspended in 200 ml of water, into which 55 g (0.59 mol) of methyl chloroformate and a solution of 21.5 g (0.51 mol) of sodium hydroxide in 60 ml of water were poured together at 10° C. or lower, and the mixture was stirred at the same temperature for 2 hours. The precipitated crystals were collected by filtration, washed with water, and dried in a vacuum oven, which afforded 111.6 g (0.45 mol) of methyl 2-bromo-4-fluorophenoxyformate.

Then, 110 g (0.44 mol) of methyl 2-bromo-4-fluorophenoxyformate was dissolved in 250 ml of sulfuric acid, to which a mixed acid of 30 g of fuming nitric acid and 30 ml of sulfuric acid was added dropwise at 5° C. or lower, and the mixture was stirred for 2 hours. The reaction mixture was poured onto ice, and the precipitated crystals were collected by filtration, washed with water, and dried, which afforded 126 g (0.43 mol) of methyl 2-bromo-4-fluoro-5-nitrophenoxyformate.

Then, 125 g (0.43 mol) of methyl 2-bromo-4-fluoro-5-nitrophenoxyformate was suspended in 200 ml of water, to which 19 g (0.47 mol) of sodium hydroxide was added, and the mixture was stirred at 50° to 60° C. for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and washed with chloroform. The aqueous layer was acidified with aqueous hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was dried and concentrated, which afforded 104 g (0.43 mol) of 2-bromo-4-fluoro-5-nitrophenol.

Then, 100 g (0.42 mol) of 2-bromo-4-fluoro-5-nitrophenol was dissolved in 400 ml of dimethylformamide, to which 70 g (0.50 mol) of potassium carbonate was added and after warming to 50° C., 94 g (0.55 mol) of isopropyl iodide was added dropwise, and the mixture was stirred at 45° to 50° C. for 1 hour. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and then with diluted hydrochloric acid, dried, and concentrated. The residue was subjected to column chromatography, which afforded 99.8 g (0.36 mol) of 2-bromo-4-fluoro-5-nitrophenyl isopropyl ether.

Then, 60 g (0.22 mol) of 2-bromo-4-fluoro-5-nitrophenyl isopropyl ether was dissolved in 300 ml of ethyl acetate, to which 1.0 g of 10% palladium-carbon was added, and the hydrogenation was effected under an atmosphere of hydrogen. After completion of the reaction, the palladium-carbon was removed by filtration, and the filtrate was concentrated, which afforded 52 g (0.21 mol) of 4-bromo-2-fluoro-5-isopropoxyaniline.

Then, 108 g (0.57 mol) of tin (II) chloride was dissolved in 100 ml of concentrated hydrochloric acid, followed by cooling to −30° C., to which a diazonium solution prepared from 47 g (0.19 mol) of 4-bromo-2-fluoro-5-isopropoxyaniline, 13.5 g (0.20 mol) of sodium nitrite, and 120 ml of hydrochloric acid was added dropwise at 0° C. or lower, and the mixture was stirred at room temperature for 2 hours. The precipitated crystals were collected by filtration and dried in a vacuum oven to give 45 g (0.14 mol) of the crude product, 4-bromo-2-fluoro-5-isopropoxyphenylhydrazine hydrochloride.

PRODUCTION EXAMPLE 28

(Production of Compound 1-1783)

First, 19 g (52.4 mmol) of carbethoxyethylidenetriphenylphosphorane and 19 g (63.2 mmol) of 3,3,3-trifluoro-2-oxopropanal 1-(4-bromo-2-fluoro-5-isopropoxyphenylhydrazone) were heated under reflux in 100 ml of THF for 5 hours. After completion of the reaction, the reaction mixture was concentrated, and the residue was subjected to silica gel chromatography, which afforded 9.1 g (22.2 mmol) of compound 1-1783.

PRODUCTION EXAMPLE 29

(Production of Compound 1-1748)

This example followed the procedures of Production Example 27, except that 41 g (0.41 mol) of 2,4-dichloro-5-isopropoxyphenylhydrazine hydrochloride was used in place of 4-bromo-2-fluoro-5-isopropoxyphenylhydrazine hydrochloride, which afforded 31.3 g (91.3 mmol) of 3,3,3-trifluoro-2-oxopropanal 1-(2,4-dichloro-5-isopropoxyphenylhydrazone). Then, this compound and 40 g (0.11 mol) of carbethoxyethylidenetriphenylphosphorane were heated under reflux in 100 ml of THF for 5 hours. After completion of the reaction, the reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography, which afforded 21 g (54.8 mmol) of compound 1-1748.

The 2,4-dichloro-5-isopropoxyphenylhydrazine hydrochloride used above was produced from 2,4-dichlorophenol by the same process as shown in Reference Example 3.

PRODUCTION EXAMPLE 30

(Production of Compound 1-1029)

First, 9 g (22.8 mmol) of 2-(4-bromo-2-fluoro-5-isopropyloxyphenyl)-5-trifluoromethylpyridazin-3-one was added to 50 ml of sulfuric acid, and the mixture was stirred for 1 hour. After completion of the reaction, the reaction mixture was poured onto ice and extracted with ethyl acetate. The ethyl acetate layer was dried and concentrated, and the residue was subjected to column chromatography (eluent, hexane:ethyl acetate=5:1), which afforded 5.9 g (16.7 mmol) of compound 1-1029.

PRODUCTION EXAMPLE 31

(Production of Compound 1-392)

First, 9 g (22.0 mmol) of 2-(4-bromo-2-fluoro-5-isopropyloxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one was added to 50 ml of sulfuric acid, and the mixture was stirred for 1 hour. After completion of the reaction, the reaction mixture was poured onto ice and extracted with ethyl acetate. The ethyl acetate layer was dried and concentrated, and the residue was subjected to column chromatography (eluent, hexane:ethyl acetate=5:1), which afforded 4.2 g (11.5 mmol) of compound 1-392.

PRODUCTION EXAMPLE 32

(Production of Compound 1-1274)

First, 7.4 g (90.2 mmol) of sodium acetate and 8.0 g (28.2 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone were mixed with 70 ml of water, and the mixture was stirred at 80° C. for 30 minutes and then cooled, to which 7.0 g of ethyl 2-chloro-5-hydrazinocinnamate was added at 10° C. or lower, and the mixture was stirred for 3 hours. The precipitated crystals were collected by filtration and dried, which afforded 9.6 g (27.5 mmol) of ethyl 2-chloro-5-(3,3,3-trifluoro-2-oxopropylidenehydrazino)cinnamate.

¹H-NMR (250 MHz, CDCl₃, TMS δ (ppm)) 1.36 (3H, t, J=6.9 Hz), 4.30 (2H, q, J=6.9 Hz), 6.4-6.6 (1H, m), 7.2-7.5 (3H, m), 7.65 (1H, d, J=2.5 Hz), 8.0-8.1 (1H, m)

Then, 1.0 g (2.9 mmol) of carbethoxymethylenetriphenylphosphorane and 1.0 g (2.9 mmol) of ethyl 2-chloro-5-(3,3,3-trifluoro-2-oxopropylidenehydrazino)cinnamate were stirred in 10 ml of THF at room temperature for 1 hour. After completion of the reaction, the reaction mixture was concentrated, and the residue was subjected to column chromatography (eluent, hexane:ethyl acetate=5:1), which afforded 0.43 g (11.5 mmol) of compound 1-1274.

Reference Example 4

The ethyl 2-chloro-5-hydrazinocinnamate used in Production Example 32 was produced by the following process.

First, 60 g of tin (II) chloride was dissolved in 60 ml of concentrated hydrochloric acid, and the mixture was cooled to −30° C., to which a diazonium solution prepared from 19 g of ethyl 5-amino-2-chlorocinnamate and 6.3 g of sodium nitrite was added dropwise at 0° C. or lower. The reaction mixture was stirred at room temperature for 1 hour, and the precipitated crystals were collected by filtration. These crystals were added to ice-water, neutralized with 2N aqueous sodium hydroxide, and extracted with chloroform. The chloroform layer was dried and concentrated, which afforded 7.0 g of ethyl 2-chloro-5-hydrazinocinnamate.

PRODUCTION EXAMPLE 33

(Production of Compound 1-637)

First, 1.1 g (2.9 mmol) of carbethoxyethylidenetriphenylphosphorane and 1.0 g (2.9 mmol) of ethyl 2-chloro-5-(3,3,3-trifluoro-2-oxopropylidenehydrazino)cinnamate were heated under reflux in 10 ml of THF for 3 hours. After completion of the reaction, the reaction mixture was concentrated, and the residue was subjected to column chromatography (eluent, hexane:ethyl acetate=5:1), which afforded 0.66 g (1.7 mmol) of compound 1-637.

PRODUCTION EXAMPLE 34

(Production of Compound 1-367)

First, 0.5 g (1.6 mmol) of compound 1-353 was dissolved in 1.5 ml of pyridine, to which 0.2 g (1.7 mmol) of methanesulfonyl chloride was added dropwise, followed by stirring for 2 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The ethyl acetate layer was washed with diluted hydrochloric acid, dried, and concentrated. The residue was subjected to column chromatography (eluent, hexane:ethyl acetate ═3:1), which afforded 0.42 g (1.1 mmol) of compound 1-367.

PRODUCTION EXAMPLE 35

(Production of Compound 1-369)

This example followed the procedures of Production Example 34, except that 0.23 g (1.6 mmol) of chloromethylsulfonyl chloride was used in place of methanesulfonyl chloride, which afforded 0.38 g (0.91 mmol) of compound 1-369.

PRODUCTION EXAMPLE 36

(Production of Compound 1-39 1)

First, 32.3 g of 5-amino-2-chloro-4-fluorophenol was mixed with 150 ml of concentrated hydrochloric acid, and the mixture was stirred at 50° C. for 30 minutes, to which a solution of 15 g of sodium nitrite dissolved in 40 ml of water was added dropwise at 0° C. over 10 minutes. After stirring at 0° C. for 1 hour, the mixture was cooled to −50° C. Then, a solution of 132 g of tin (II) chloride dissolved in 132 g of concentrated sulfuric acid was rapidly added dropwise at −50° C., and the mixture was gradually warmed to room temperature and stirred for 1 hour. The solids formed were collected by filtration and dried at 80° C. under reduced pressure to give 75 g of the crude 2-fluoro-4-chloro-5-hydroxyphenylhydrazine hydrochloride crystals.

¹H-NMR (DMSO-d₆, TMS δ (ppm)) 3-5 (2H, br), 6.73 (1H, d), 7.22 (1H, d), 8.20 (1H, s), 9-11 (2H, br)

Then, 49.2 g of sodium acetate and 40.5 g of 1,1-dibromo-3,3,3-trifluoroacetone were dissolved in 400 ml of water, and the solution was heated at 80° to 90° C. for 40 minutes. The solution was cooled to 0° C., to which 75 g of the crude 2-fluoro-4-chloro-5-hydroxyphenylhydrazine hydrochloride crystals obtained above was added, and the mixture was stirred at room temperature for 70 minutes. The precipitated crystals were collected by filtration and dried under reduced pressure, which afforded 35.4 g of 3,3,3-trifluoro-2-oxopropanal 1-(4-chloro-2-fluoro-5-hydroxyphenylhydrazone).

¹H-NMR (300 MHz, CDCl₃, TMS δ (ppm)) 5.49 (1H, s), 7.15 (1H, d, J=10.5 Hz), 7.25 (1H, d, J=7.4 Hz), 7.38 (1H, q, J=1.8 Hz), 8.75 (1H, s)

Then, 12.9 g of 3,3,3-trifluoro-2-oxopropanal 1-(4-chloro-2-fluoro-5-hydroxyphenylhydrazone) and 22.3 g of carbethoxyethylidenetriphenylphosphorane were dissolved in 110 ml of tetrahydrofuran, and the solution was heated under reflux for 3 hours. The solvent was distilled out under reduced pressure, and the residue was subjected to silica gel chromatography, which afforded 8.8 g of 2-(2-fluoro-4-chloro-5-hydroxyphenyl)-4-methyl-5-trifluoromethylpyridazin-3-one (compound 1-391).

The 5-amino-2-chloro-4-fluorophenol used above can be produced by the method described in the publication of European Patent Application, EP-61741-A.

PRODUCTION EXAMPLE 37

(Production of Compound 1-332)

First, 2 g of 3,3,3-trifluoro-2-oxo-1-propanal 1-(4-chlorophenylhydrazone) and 2 g of ethyl diethylphosphonoacetate were mixed with 20 ml of triethylamine, and the reaction was allowed to proceed at 50° C. for 24 hours. The solvent was distilled out under reduced pressure, and the residue was subjected to column chromatography, which afforded 1.16 g of 2-(4-chlorophenyl)-5-trifluoromethylpyridazin-3-one (compound 1-332).

Reference Example 5

The 3,3,3-trifluoro-2-oxopropanal 1-(4-chloro-2-fluoro-5-isopropoxyphenylhydrazone) produced in Production Example 19 can also be produced by the following process.

First, 20.1 g of ethyl 4,4,4-trifluoroacetoacetate and 25 g of sodium acetate were dissolved in 150 ml of water, to which a diazonium solution in hydrochloric acid prepared from 20.3 g of 4-chloro-2-fluoro-5-isopropoxyaniline, 20 ml of concentrated hydrochloric acid, 20 ml of water, and 7.35 g of sodium nitrite was added dropwise at 10° C. or lower. After stirring at room temperature for 1 hour, the precipitated crystals were collected by filtration, washed with water, and dried, which afforded 34 g of the desired product as orange crystals (yield, 85%).

Then, 15.9 g of the ester obtained above and 1.7 g of lithium hydroxide monohydrate were added to 30 ml of 1,4-dioxane and 3 ml of water, and the mixture was heated under reflux for 6 hours. The reaction mixture was poured into ice-water, neutralized with diluted hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was dried and concentrated, and the precipitated crystals were washed with hexane, which afforded 11.3 g of the desired product as yellow crystals (yield, 76.3%).

Then, 7.4 g of the carboxylic acid obtained above was dissolved in 42 ml of N,N-dimethylformamide, and the reaction solution was heated to 100° C. and kept at the same temperature for 30 minutes. Thereafter, the reaction solution was cooled to room temperature, poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with diluted hydrochloric acid, dried with magnesium sulfate, and concentrated, which afforded 5.9 g of the desired product as orange crystals (yield, 90%).

¹H-NMR (250 MHz, CDCl₃, TMS δ (ppm)) 1.39 (6H, d, J=6.0 Hz), 4.38-4.52 (1H, m), 7.15 (1H, d, J=10.5 Hz), 7.22 (1H, d, J=7.3 Hz), 7.43 (1H, q, J=1.7 Hz), 9.18 (1H, br)

Reference Example 6

In the same manner as described in Reference Example 2,3,3,3-trifluoro-2-oxopropanal 4-chlorophenylhydrazone was produced.

First, 5.0 g of the ester as the starting material and 0.67 g of lithium hydroxide monohydrate were added to a mixed solution of 30 ml of 1,4-dioxane and 2 ml of water, and the mixture was heated under reflux for 1.5 hours. The reaction mixture was poured into ice-water, neutralized with diluted hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was dried with magnesium sulfate and concentrated, and the precipitated crystals were washed with a mixed solvent of hexane and diethyl ether (hexane:diethyl ether=2:1), which afforded 3.3 g of the desired compound as yellow crystals (yield, 73%).

Process 1) A solution prepared by dissolving 3.3 g of the carboxylic acid obtained by the above reaction in 10 ml of dimethylsulfoxide was heated to 100° C. and kept at the same temperature for 10 minutes, followed by cooling to room temperature. Thereafter, the reaction mixture was subjected to silica gel chromatography (eluent, hexane:ethyl acetate=7:1), which afforded 2.55 g of the desired product (yield, 91%).

Process 2) A reaction mixture prepared by adding 5.0 g of the carboxylic acid obtained by the above reaction, 0.5 ml of quinoline, and 0.1 g of copper powder to 40 ml of toluene was heated to 100° C. and kept at the same temperature for 20 minutes. After completion of the reaction, the reaction mixture was cooled to room temperature and subjected to silica gel chromatography (eluent, hexane:ethyl acetate=8:1), which afforded 3.6 g of the desired product (yield, 86%).

Some of the present compounds are shown with their compound numbers in Tables 1 to 5, where the symbol “n” refers to normal-; “i”, iso-; “s”, secondary-; and “c”, cyclo-.

TABLE 1 Compounds of the formula:

Compound No. X Y R³ R¹ R² B 1-1 H F H CF₂Cl H H 1-2 H Cl H CF₂Cl H H 1-3 H Br H CF₂Cl H H 1-4 H F H CF₂Cl CH₃ H 1-5 H Cl H CF₂Cl CH₃ H 1-6 H Br H CF₂Cl CH₃ H 1-7 F F H CF₂Cl H H 1-8 F Cl H CF₂Cl H H 1-9 F Br H CF₂Cl H H 1-10 F F H CF₂Cl CH₃ H 1-11 F Cl H CF₂Cl CH₃ H 1-12 F Br H CF₂Cl CH₃ H 1-13 H F H CF₂Cl CH₃ NO₂ 1-14 H Cl H CF₂Cl CH₃ NO₂ 1-15 H Br H CF₂Cl CH₃ NO₂ 1-16 F F H CF₂Cl CH₃ NO₂ 1-17 F Cl H CF₂Cl CH₃ NO₂ 1-18 F Br H CF₂Cl CH₃ NO₂ 1-19 H F H CF₂Cl CH₃ NH₂ 1-20 H Cl H CF₂Cl CH₃ NH₂ 1-21 H Br H CF₂Cl CH₃ NH₂ 1-22 F F H CF₂Cl CH₃ NH₂ 1-23 F Cl H CF₂Cl CH₃ NH₂ 1-24 F Br H CF₂Cl CH₃ NH₂ 1-25 H F H CF₂Cl CH₃ OH 1-26 H Cl H CF₂Cl CH₃ OH 1-27 H Br H CF₂Cl CH₃ OH 1-28 F F H CF₂Cl CH₃ OH 1-29 F Cl H CF₂Cl CH₃ OH 1-30 F Br H CF₂Cl CH₃ OH 1-31 H Cl H CF₂Cl CH₃ NHCH₃ 1-32 H Cl H CF₂Cl CH₃ NHC₂H₅ 1-33 H Cl H CF₂Cl CH₃ NHCH₂CH═CH₂ 1-34 H Cl H CF₂Cl CH₃ NHCH₂C≡CH 1-35 H Cl H CF₂Cl CH₃ NHCH(CH₃)C≡CH 1-36 H Cl H CF₂Cl CH₃ NHSO₂CH₃ 1-37 H Cl H CF₂Cl CH₃ NHSO₂C₂H₅ 1-38 H Cl H CF₂Cl CH₃ NHSO₂CH₂Cl 1-39 H Cl H CF₂Cl CH₃ NHSO₂CF₃ 1-40 H Cl H CF₂Cl CH₃ N(CH₃)SO₂CH₃ 1-41 H Cl H CF₂Cl CH₃ N(CH₂C≡CH)SO₂CH₃ 1-42 H Cl H CF₂Cl CH₃ NHCOOCH₃ 1-43 H Cl H CF₂Cl CH₃ NHCOOC₂H₅ 1-44 H Cl H CF₂Cl CH₃ NHCOO^(n)C₃H₇ 1-45 H Cl H CF₂Cl CH₃ NHCOO^(i)C₃H₇ 1-46 H Cl H CF₂Cl CH₃ NHCOO^(n)C₄H₉ 1-47 H Cl H CF₂Cl CH₃ NHCOO^(n)C₅H₁₁ 1-48 H Cl H CF₂Cl CH₃ NHCH₂COOCH₃ 1-49 H Cl H CF₂Cl CH₃ NHCH₂COOC₂H₅ 1-50 H Cl H CF₂Cl CH₃ NHCH₂COO^(n)C₃H₇ 1-51 H Cl H CF₂Cl CH₃ NHCH₂COO^(n)C₄H₉ 1-52 H Cl H CF₂Cl CH₃ NHCH₂COO^(n)C₅H₁₁ 1-53 H Cl H CF₂Cl CH₃ NHCH₂COO^(i)C₃H₇ 1-54 H Cl H CF₂Cl CH₃ NHCH₂COO^(c)C₅H₉ 1-55 H Cl H CF₂Cl CH₃ NHCH₂COO^(c)C₆H₁₁ 1-56 H Cl H CF₂Cl CH₃ NHCH(CH₃)COOCH₃ 1-57 H Cl H CF₂Cl CH₃ NHCH(CH₃)COOC₂H₅ 1-58 H Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(n)C₃H₇ 1-59 H Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(n)C₄H₉ 1-60 H Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(n)C₅H₁₁ 1-61 H Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(i)C₃H₇ 1-62 H Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(c)C₅H₉ 1-63 H Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(c)C₆H₁₁ 1-64 F Cl H CF₂Cl CH₃ NHCH₃ 1-65 F Cl H CF₂Cl CH₃ NHC₂H₅ 1-66 F Cl H CF₂Cl CH₃ NHCH₂CH═CH₂ 1-67 F Cl H CF₂Cl CH₃ NHCH₂C≡CH 1-68 F Cl H CF₂Cl CH₃ NHCH(CH₃)C≡CH 1-69 F Cl H CF₂Cl CH₃ NHSO₂CH₃ 1-70 F Cl H CF₂Cl CH₃ NHSO₂C₂H₅ 1-71 F Cl H CF₂Cl CH₃ NHSO₂CH₂Cl 1-72 F Cl H CF₂Cl CH₃ NHSO₂CF₃ 1-73 F Cl H CF₂Cl CH₃ N(CH₃)SO₂CH₃ 1-74 F Cl H CF₂Cl CH₃ N(CH₂C≡CH)SO₂CH₃ 1-75 F Cl H CF₂Cl CH₃ NHCOOCH₃ 1-76 F Cl H CF₂Cl CH₃ NHCOOC₂H₅ 1-77 F Cl H CF₂Cl CH₃ NHCOO^(n)C₃H₇ 1-78 F Cl H CF₂Cl CH₃ NHCOO^(i)C₃H₇ 1-79 F Cl H CF₂Cl CH₃ NHCOO^(n)C₄H₉ 1-80 F Cl H CF₂Cl CH₃ NHCOO^(n)C₅H₁₁ 1-81 F Cl H CF₂Cl CH₃ NHCH₂COOCH₃ 1-82 F Cl H CF₂Cl CH₃ NHCH₂COOC₂H₅ 1-83 F Cl H CF₂Cl CH₃ NHCH₂COO^(n)C₃H₇ 1-84 F Cl H CF₂Cl CH₃ NHCH₂COO^(n)C₄H₉ 1-85 F Cl H CF₂Cl CH₃ NHCH₂COO^(n)C₅H₁₁ 1-86 F Cl H CF₂Cl CH₃ NHCH₂COO^(i)C₃H₇ 1-87 F Cl H CF₂Cl CH₃ NHCH₂COO^(c)C₅H₉ 1-88 F Cl H CF₂Cl CH₃ NH₂CH₂COO^(c)C₆H₁₁ 1-89 F Cl H CF₂Cl CH₃ NHCH(CH₃)COOCH₃ 1-90 F Cl H CF₂Cl CH₃ NHCH(CH₃)COOC₂H₅ 1-91 F Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(n)C₃H₇ 1-92 F Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(n)C₄H₉ 1-93 F Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(n)C₅H₁₁ 1-94 F Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(i)C₃H₇ 1-95 F Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(c)C₅H₉ 1-96 F Cl H CF₂Cl CH₃ NHCH(CH₃)COO^(c)C₆H₁₁ 1-97 H Cl H CF₂Cl CH₃ OCH₃ 1-98 H Cl H CF₂Cl CH₃ OC₂H₅ 1-99 H Cl H CF₂Cl CH₃ O^(i)C₃H₇ 1-100 H Cl H CF₂Cl CH₃ O^(n)C₃H₇ 1-101 H Cl H CF₂Cl CH₃ OCH₂CH₂Cl 1-102 H Cl H CF₂Cl CH₃ OCF₂CF₂H 1-103 H Cl H CF₂Cl CH₃ O^(c)C₅H₉ 1-104 H Cl H CF₂Cl CH₃ O^(c)C₆H₁₁ 1-105 H Cl H CF₂Cl CH₃ OCH₂CH═CH₂ 1-106 H Cl H CF₂Cl CH₃ OCH₂CCl═CH₂ 1-107 H Cl H CF₂Cl CH₃ OCH₂CCl═CHCl 1-108 H Cl H CF₂Cl CH₃ OCH(CH₃)CH═CH₂ 1-109 H Cl H CF₂Cl CH₃ OCH₂C≡CH 1-110 H Cl H CF₂Cl CH₃ OCH(CH₃)C≡CH 1-111 H Cl H CF₂Cl CH₃ OCH₂C≡CBr 1-112 H Cl H CF₂Cl CH₃ OCH₂C≡CCl 1-113 H Cl H CF₂Cl CH₃ OCH₂C≡CCH₂Cl 1-114 H Cl H CF₂Cl CH₃ OCH₂CN 1-115 H Cl H CF₂Cl CH₃ OCH₂OCH₃ 1-116 H Cl H CF₂Cl CH₃ OCH₂OC₂H₅ 1-117 H Cl H CF₂Cl CH₃ OCH₂SCH₃ 1-118 H Cl H CF₂Cl CH₃ OCH₂COOCH₃ 1-119 H Cl H CF₂Cl CH₃ OCH₂COOC₂H₅ 1-120 H Cl H CF₂Cl CH₃ OCH₂COO^(n)C₃H₇ 1-121 H Cl H CF₂Cl CH₃ OCH₂COO^(n)C₄H₉ 1-122 H Cl H CF₂Cl CH₃ OCH₂COO^(n)C₅H₁₁ 1-123 H Cl H CF₂Cl CH₃ OCH₂COO^(i)C₃H₇ 1-124 H Cl H CF₂Cl CH₃ OCH₂COO^(c)C₅H₉ 1-125 H Cl H CF₂Cl CH₃ OCH₂COO^(c)C₆H₁₁ 1-126 H Cl H CF₂Cl CH₃ OCH(CH₃)COOCH₃ 1-127 H Cl H CF₂Cl CH₃ OCH(CH₃)COOC₂H₅ 1-128 H Cl H CF₂Cl CH₃ OCH(CH₃)COO^(n)C₃H₇ 1-129 H Cl H CF₂Cl CH₃ OCH(CH₃)COO^(n)C₄H₉ 1-130 H Cl H CF₂Cl CH₃ OCH(CH₃)COO^(n)C₅H₁₁ 1-131 H Cl H CF₂Cl CH₃ OCH(CH₃)COO^(i)C₃H₇ 1-132 H Cl H CF₂Cl CH₃ OCH(CH₃)COO^(c)C₅H₉ 1-133 H Cl H CF₂Cl CH₃ OCH(CH₃)COO^(c)C₆H₁₁ 1-134 H Cl H CF₂Cl CH₃ OCH₂CON(CH₃)₂ 1-135 H Cl H CF₂Cl CH₃ OCH₂CON(C₂H₅)₂ 1-136 H Cl H CF₂Cl CH₃ OCH₂CON(CH₃)C₂H₅ 1-137 H Cl H CF₂Cl CH₃ OCH(CH₃)CON(CH₃)₂ 1-138 H Cl H CF₂Cl CH₃ OCH(CH₃)CON(C₂H₅)₂ 1-139 H Cl H CF₂Cl CH₃ OCH(CH₃)CON(CH₃)C₂H₅ 1-140 H Cl H CF₂Cl CH₃ OCH₂COON(CH₃)₂ 1-141 H Cl H CF₂Cl CH₃ OCH₂COON(C₂H₅)₂ 1-142 H Cl H CF₂Cl CH₃ OCH(CH₃)COON(CH₃)₂ 1-143 H Cl H CF₂Cl CH₃ OCH(CH₃)COON(C₂H₅)₂ 1-144 F Cl H CF₂Cl CH₃ OCH₃ 1-145 F Cl H CF₂Cl CH₃ OC₂H₅ 1-146 F Cl H CF₂Cl CH₃ O^(i)C₃H₇ 1-147 F Cl H CF₂Cl CH₃ O^(n)C₃H₇ 1-148 F Cl H CF₂Cl CH₃ OCH₂CH₂Cl 1-149 F Cl H CF₂Cl CH₃ OCF₂CF₂H 1-150 F Cl H CF₂Cl CH₃ O^(c)C₅H₉ 1-151 F Cl H CF₂Cl CH₃ O^(c)C₆H₁₁ 1-152 F Cl H CF₂Cl CH₃ OCH₂CH₂═CH₂ 1-153 F Cl H CF₂Cl CH₃ OCH₂CCl═CH₂ 1-154 F Cl H CF₂Cl CH₃ OCH₂CCl═CHCl 1-155 F Cl H CF₂Cl CH₃ OCH(CH₃)CH═CH₂ 1-156 F Cl H CF₂Cl CH₃ OCH₂C≡CH 1-157 F Cl H CF₂Cl CH₃ OCH(CH₃)C≡CH 1-158 F Cl H CF₂Cl CH₃ OCH₂C≡CBr 1-159 F Cl H CF₂Cl CH₃ OCH₂C≡CCl 1-160 F Cl H CF₂Cl CH₃ OCH₂C≡CCH₂Cl 1-161 F Cl H CF₂Cl CH₃ OCH₂CN 1-162 F Cl H CF₂Cl CH₃ OCH₂OCH₃ 1-163 F Cl H CF₂Cl CH₃ OCH₂OC₂H₅ 1-164 F Cl H CF₂Cl CH₃ OCH₂SCH₃ 1-165 F Cl H CF₂Cl CH₃ OCH₂COOCH₃ 1-166 F Cl H CF₂Cl CH₃ OCH₂COOC₂H₅ 1-167 F Cl H CF₂Cl CH₃ OCH₂COO^(n)C₃H₇ 1-168 F Cl H CF₂Cl CH₃ OCH₂COO^(n)C₄H₉ 1-169 F Cl H CF₂Cl CH₃ OCH₂COO^(n)C₅H₁₁ 1-170 F Cl H CF₂Cl CH₃ OCH₂COO^(i)C₃H₇ 1-171 F Cl H CF₂Cl CH₃ OCH₂COO^(c)C₅H₉ 1-172 F Cl H CF₂Cl CH₃ OCH₂COO^(c)C₆H₁₁ 1-173 F Cl H CF₂Cl CH₃ OCH(CH₃)COOCH₃ 1-174 F Cl H CF₂Cl CH₃ OCH(CH₃)COOC₂H₅ 1-175 F Cl H CF₂Cl CH₃ OCH(CH₃)COO^(n)C₃H₇ 1-176 F Cl H CF₂Cl CH₃ OCH(CH₃)COO^(n)C₄H₉ 1-177 F Cl H CF₂Cl CH₃ OCH(CH₃)COO^(n)C₅H₁₁ 1-178 F Cl H CF₂Cl CH₃ OCH(CH₃)COO^(i)C₃H₇ 1-179 F Cl H CF₂Cl CH₃ OCH(CH₃)COO^(c)C₅H₉ 1-180 F Cl H CF₂Cl CH₃ OCH(CH₃)COO^(c)C₆H₁₁ 1-181 F Cl H CF₂Cl CH₃ OCH₂CON(CH₃)₂ 1-182 F Cl H CF₂Cl CH₃ OCH₂CON(C₂H₅)₂ 1-183 F Cl H CF₂Cl CH₃ OCH₂CON(CH₃)C₂H₅ 1-184 F Cl H CF₂Cl CH₃ OCH(CH₃)CON(CH₃)₂ 1-185 F Cl H CF₂Cl CH₃ OCH(CH₃)CON(C₂H₅)₂ 1-186 F Cl H CF₂Cl CH₃ OCH(CH₃)CON(CH₃)C₂H₅ 1-187 F Cl H CF₂Cl CH₃ OCH₂COON(CH₃)₂ 1-188 F Cl H CF₂Cl CH₃ OCH₂COON(C₂H₅)₂ 1-189 F Cl H CF₂Cl CH₃ OCH(CH₃)COON(CH₃)₂ 1-190 F Cl H CF₂Cl CH₃ OCH(CH₃)COON(C₂H₅)₂ 1-191 H F H CF₂Cl CH₃ SH 1-192 H Cl H CF₂Cl CH₃ SH 1-193 H Br H CF₂Cl CH₃ SH 1-194 F F H CF₂Cl CH₃ SH 1-195 F Cl H CF₂Cl CH₃ SH 1-196 F Br H CF₂Cl CH₃ SH 1-197 H Cl H CF₂Cl CH₃ SCH₃ 1-198 H Cl H CF₂Cl CH₃ SC₂H₅ 1-199 H Cl H CF₂Cl CH₃ S^(i)C₃H₇ 1-200 H Cl H CF₂Cl CH₃ SCH₂CH₂Cl 1-201 H Cl H CF₂Cl CH₃ S^(c)C₅H₉ 1-202 H Cl H CF₂Cl CH₃ S^(c)C₆H₁₁ 1-203 H Cl H CF₂Cl CH₃ SCH₂CH═CH₂ 1-204 H Cl H CF₂Cl CH₃ SCH₂CCl═CH₂ 1-205 H Cl H CF₂Cl CH₃ SCH₂CCl═CHCl 1-206 H Cl H CF₂Cl CH₃ SCH(CH₃)CH═CH₂ 1-207 H Cl H CF₂Cl CH₃ SCH₂C≡CH 1-208 H Cl H CF₂Cl CH₃ SCH(CH₃)C≡CH 1-209 H Cl H CF₂Cl CH₃ SCH₂COOCH₃ 1-210 H Cl H CF₂Cl CH₃ SCH₂COOC₂H₅ 1-211 H Cl H CF₂Cl CH₃ SCH₂COO^(n)C₃H₇ 1-212 H Cl H CF₂Cl CH₃ SCH₂COO^(n)C₄H₉ 1-213 H Cl H CF₂Cl CH₃ SCH₂COO^(n)C₅H₁₁ 1-214 H Cl H CF₂Cl CH₃ SCH₂COO^(i)C₃H₇ 1-215 H Cl H CF₂Cl CH₃ SCH₂COO^(c)C₅H₉ 1-216 H Cl H CF₂Cl CH₃ SCH₂COO^(c)C₆H₁₁ 1-217 H Cl H CF₂Cl CH₃ SCH(CH₃)COOCH₃ 1-218 H Cl H CF₂Cl CH₃ SCH(CH₃)COOC₂H₅ 1-219 H Cl H CF₂Cl CH₃ SCH(CH₃)COO^(n)C₃H₇ 1-220 H Cl H CF₂Cl CH₃ SCH(CH₃)COO^(n)C₄H₉ 1-221 H Cl H CF₂Cl CH₃ SCH(CH₃)COO^(n)C₅H₁₁ 1-222 H Cl H CF₂Cl CH₃ SCH(CH₃)COO^(i)C₃H₇ 1-223 H Cl H CF₂Cl CH₃ SCH(CH₃)COO^(c)C₅H₉ 1-224 H Cl H CF₂Cl CH₃ SCH(CH₃)COO^(c)C₆H₁₁ 1-225 H Cl H CF₂Cl CH₃ SCH₂CON(CH₃)₂ 1-226 H Cl H CF₂Cl CH₃ SCH₂CON(C₂H₅)₂ 1-227 H Cl H CF₂Cl CH₃ SCH₂CON(tetramethylene) 1-228 H Cl H CF₂Cl CH₃ SCH₂CON(pentamethylene) 1-229 H Cl H CF₂Cl CH₃ SCH₂CON(ethyleneoxyethylene) 1-230 H Cl H CF₂Cl CH₃ SCH(CH₃)CON(CH₃)₂ 1-231 H Cl H CF₂Cl CH₃ SCH(CH₃)CON(C₂H₅)₂ 1-232 H Cl H CF₂Cl CH₃ SCH(CH₃)CON(tetramethylene) 1-233 H Cl H CF₂Cl CH₃ SCH(CH₃)CON(pentamethylene) 1-234 F Cl H CF₂Cl CH₃ SCH₃ 1-235 F Cl H CF₂Cl CH₃ SC₂H₅ 1-236 F Cl H CF₂Cl CH₃ S^(i)C₃H₇ 1-237 F Cl H CF₂Cl CH₃ SCH₂CH₂Cl 1-238 F Cl H CF₂Cl CH₃ S^(c)C₅H₉ 1-239 F Cl H CF₂Cl CH₃ S^(c)C₆H₁₁ 1-240 F Cl H CF₂Cl CH₃ SCH₂CH═CH₂ 1-241 F Cl H CF₂Cl CH₃ SCH₂CCl═CH₂ 1-242 F Cl H CF₂Cl CH₃ SCH₂CCl═CHCl 1-243 F Cl H CF₂Cl CH₃ SCH(CH₃)CH═CH₂ 1-244 F Cl H CF₂Cl CH₃ SCH₂C≡CH 1-245 F Cl H CF₂Cl CH₃ SCH(CH₃)C≡CH 1-246 F Cl H CF₂Cl CH₃ SCH₂COOCH₃ 1-247 F Cl H CF₂Cl CH₃ SCH₂COOC₂H₅ 1-248 F Cl H CF₂Cl CH₃ SCH₂COO^(n)C₃H₇ 1-249 F Cl H CF₂Cl CH₃ SCH₂COO^(n)C₄H₉ 1-250 F Cl H CF₂Cl CH₃ SCH₂COO^(n)C₅H₁₁ 1-251 F Cl H CF₂Cl CH₃ SCH₂COO^(i)C₃H₇ 1-252 F Cl H CF₂Cl CH₃ SCH₂COO^(c)C₅H₉ 1-253 F Cl H CF₂Cl CH₃ SCH₂COO^(c)C₆H₁₁ 1-254 F Cl H CF₂Cl CH₃ SCH(CH₃)COOCH₃ 1-255 F Cl H CF₂Cl CH₃ SCH(CH₃)COOC₂H₅ 1-256 F Cl H CF₂Cl CH₃ SCH(CH₃)COO^(n)C₃H₇ 1-257 F Cl H CF₂Cl CH₃ SCH(CH₃)COO^(n)C₄H₉ 1-258 F Cl H CF₂Cl CH₃ SCH(CH₃)COO^(n)C₅H₁₁ 1-259 F Cl H CF₂Cl CH₃ SCH(CH₃)COO^(i)C₃H₇ 1-260 F Cl H CF₂Cl CH₃ SCH(CH₃)COO^(c)C₅H₉ 1-261 F Cl H CF₂Cl CH₃ SCH(CH₃)COO^(c)C₆H₁₁ 1-262 F Cl H CF₂Cl CH₃ SCH₂CON(CH₃)₂ 1-263 F Cl H CF₂Cl CH₃ SCH₂CON(C₂H₅)₂ 1-264 F Cl H CF₂Cl CH₃ SCH₂CON(tetramethylene) 1-265 F Cl H CF₂Cl CH₃ SCH₂CON(pentamethylene) 1-266 F Cl H CF₂Cl CH₃ SCH₂CON(ethyleneoxyethylene) 1-267 F Cl H CF₂Cl CH₃ SCH(CH₃)CON(CH₃)₂ 1-268 F Cl H CF₂Cl CH₃ SCH(CH₃)CON(C₂H₅)₂ 1-269 F Cl H CF₂Cl CH₃ SCH(CH₃)CON(tetramethylene) 1-270 F Cl H CF₂Cl CH₃ SCH(CH₃)CON(pentamethylene) 1-271 H F H CF₂Cl CH₃ SO₂Cl 1-272 H Cl H CF₂Cl CH₃ SO₂Cl 1-273 H Br H CF₂Cl CH₃ SO₂Cl 1-274 F F H CF₂Cl CH₃ SO₂Cl 1-275 F Cl H CF₂Cl CH₃ SO₂Cl 1-276 F Br H CF₂Cl CH₃ SO₂Cl 1-277 H Cl H CF₂Cl CH₃ SO₂OCH₃ 1-278 H Cl H CF₂Cl CH₃ SO₂OC₂H₅ 1-279 H Cl H CF₂Cl CH₃ SO₂O^(i)C₃H₇ 1-280 H Cl H CF₂Cl CH₃ SO₂OCH₂CH═CH₂ 1-281 F Cl H CF₂Cl CH₃ SO₂OCH₃ 1-282 F Cl H CF₂Cl CH₃ SO₂OC₂H₅ 1-283 F Cl H CF₂Cl CH₃ SO₂O^(i)C₃H₇ 1-284 F Cl H CF₂Cl CH₃ SO₂OCH₂CH═CH₂ 1-285 H Cl H CF₂Cl CH₃ SO₂N(CH₃)₂ 1-286 H Cl H CF₂Cl CH₃ SO₂N(C₂H₅)₂ 1-287 F Cl H CF₂Cl CH₃ SO₂N(CH₃)₂ 1-288 F Cl H CF₂Cl CH₃ SO₂N(C₂H₅)₂ 1-289 H Cl H CF₂Cl CH₃ COOH 1-290 H Cl H CF₂Cl CH₃ COOCH₃ 1-291 H Cl H CF₂Cl CH₃ COOC₂H₅ 1-292 H Cl H CF₂Cl CH₃ COO^(n)C₃H₇ 1-293 H Cl H CF₂Cl CH₃ COO^(n)C₄H₉ 1-294 H Cl H CF₂Cl CH₃ COO^(n)C₅H₁₁ 1-295 H Cl H CF₂Cl CH₃ COO^(i)C₃H₇ 1-296 H Cl H CF₂Cl CH₃ COOCH₂CH₂Cl 1-297 H Cl H CF₂Cl CH₃ COOCH₂CH₂Br 1-298 H Cl H CF₂Cl CH₃ CON(CH₃)₂ 1-299 H Cl H CF₂Cl CH₃ CONHCH₃ 1-300 H Cl H CF₂Cl CH₃ CON(C₂H₅)₂ 1-301 H Cl H CF₂Cl CH₃ CONHC₂H₅ 1-302 H Cl H CF₂Cl CH₃ COCH₃ 1-303 H Cl H CF₂Cl CH₃ COC₂H₅ 1-304 H Cl H CF₂Cl CH₃ COCH₂Cl 1-305 H Cl H CF₂Cl CH₃ CHO 1-306 H Cl H CF₂Cl CH₃ CH═CHCOOCH₃ 1-307 H Cl H CF₂Cl CH₃ CH═CHCOOC₂H₅ 1-308 H Cl H CF₂Cl CH₃ CH₂CH₂COOCH₃ 1-309 H Cl H CF₂Cl CH₃ CH₂CH₂COOC₂H₅ 1-310 F Cl H CF₂Cl CH₃ COOH 1-311 F Cl H CF₂Cl CH₃ COOCH₃ 1-312 F Cl H CF₂Cl CH₃ COOC₂H₅ 1-313 F Cl H CF₂Cl CH₃ COO^(n)C₃H₇ 1-314 F Cl H CF₂Cl CH₃ COO^(n)C₄H₉ 1-315 F Cl H CF₂Cl CH₃ COO^(n)C₅H₁₁ 1-316 F Cl H CF₂Cl CH₃ COO^(i)C₃H₇ 1-317 F Cl H CF₂Cl CH₃ COOCH₂CH₂Cl 1-318 F Cl H CF₂Cl CH₃ COOCH₂CH₂Br 1-319 F Cl H CF₂Cl CH₃ CON(CH₃)₂ 1-320 F Cl H CF₂Cl CH₃ CONHCH₃ 1-321 F Cl H CF₂Cl CH₃ CON(C₂H₅)₂ 1-322 F Cl H CF₂Cl CH₃ CONHC₂H₅ 1-323 F Cl H CF₂Cl CH₃ COCH₃ 1-324 F Cl H CF₂Cl CH₃ COC₂H₅ 1-325 F Cl H CF₂Cl CH₃ COCH₂Cl 1-326 F Cl H CF₂Cl CH₃ CHO 1-327 F Cl H CF₂Cl CH₃ CH═CHCOOCH₃ 1-328 F Cl H CF₂Cl CH₃ CH═CHCOOC₂H₅ 1-329 F Cl H CF₂Cl CH₃ CH₂CH₂COOCH₃ 1-330 F Cl H CF₂Cl CH₃ CH₂CH₂COOC₂H₅ 1-331 H F H CF₃ H H 1-332 H Cl H CF₃ H H 1-333 H Br H CF₃ H H 1-334 H F H CF₃ CH₃ H 1-335 H Cl H CF₃ CH₃ H 1-336 H Br H CF₃ CH₃ H 1-337 F F H CF₃ H H 1-338 F Cl H CF₃ H H 1-339 F Br H CF₃ H H 1-340 F F H CF₃ CH₃ H 1-341 F Cl H CF₃ CH₃ H 1-342 F Br H CF₃ CH₃ H 1-343 H F H CF₃ CH₃ NO₂ 1-344 H Cl H CF₃ CH₃ NO₂ 1-345 H Br H CF₃ CH₃ NO₂ 1-346 F F H CF₃ CH₃ NO₂ 1-347 F Cl H CF₃ CH₃ NO₂ 1-348 F Br H CF₃ CH₃ NO₂ 1-349 H F H CF₃ CH₃ NH₂ 1-350 H Cl H CF₃ CH₃ NH₂ 1-351 H Br H CF₃ CH₃ NH₂ 1-352 F F H CF₃ CH₃ NH₂ 1-353 F Cl H CF₃ CH₃ NH₂ 1-354 H Cl H CF₃ CH₃ NHCH(CH₃)COOCH₃ 1-355 H Cl H CF₃ CH₃ NHCH(CH₃)COOC₂H₅ 1-356 H Cl H CF₃ CH₃ NHCH(CH₃)COO^(n)C₃H₇ 1-357 H Cl H CF₃ CH₃ NHCH(CH₃)COO^(n)C₄H₉ 1-358 H Cl H CF₃ CH₃ NHCH(CH₃)COO^(n)C₅H₁₁ 1-359 H Cl H CF₃ CH₃ NHCH(CH₃)COO^(i)C₃H₇ 1-360 H Cl H CF₃ CH₃ NHCH(CH₃)COO^(c)C₅H₉ 1-361 H Cl H CF₃ CH₃ NHCH(CH₃)COO^(c)C₆H₁₁ 1-362 F Cl H CF₃ CH₃ NHCH₃ 1-363 F Cl H CF₃ CH₃ NHC₂H₅ 1-364 F Cl H CF₃ CH₃ NHCH₂CH═CH₂ 1-365 F Cl H CF₃ CH₃ NHCH₂C≡CH 1-366 F Cl H CF₃ CH₃ NHCH(CH₃)C≡CH 1-367 F Cl H CF₃ CH₃ NHSO₂CH₃ 1-368 F Cl H CF₃ CH₃ NHSO₂C₂H₅ 1-369 F Cl H CF₃ CH₃ NHSO₂CH₂Cl 1-370 F Cl H CF₃ CH₃ NHSO₂CF₃ 1-371 F Cl H CF₃ CH₃ N(CH₃)SO₂CH₃ 1-372 F Cl H CF₃ CH₃ N(CH₂C≡CH)SO₂CH₃ 1-373 F Cl H CF₃ CH₃ NHCOOCH₃ 1-374 F Cl H CF₃ CH₃ NHCOOC₂H₅ 1-375 F Cl H CF₃ CH₃ NHCOO^(n)C₃H₇ 1-376 F Cl H CF₃ CH₃ NHCOO^(i)C₃H₇ 1-377 F Cl H CF₃ CH₃ NHCOO^(n)C₄H₉ 1-378 F Cl H CF₃ CH₃ NHCOO^(n)C₅H₁₁ 1-379 F Cl H CF₃ CH₃ NHCH₂COOCH₃ 1-380 F Cl H CF₃ CH₃ NHCH₂COOC₂H₅ 1-381 F Cl H CF₃ CH₃ NHCH₂COO^(n)C₃H₇ 1-382 F Cl H CF₃ CH₃ NHCH₂COO^(n)C₄H₉ 1-383 F Cl H CF₃ CH₃ NHCH₂COO^(n)C₅H₁₁ 1-384 F Cl H CF₃ CH₃ NHCH₂COO^(i)C₃H₇ 1-385 F Cl H CF₃ CH₃ NHCH₂COO^(c)C₅H₉ 1-386 F Br H CF₃ CH₃ NH₂ 1-387 H F H CF₃ CH₃ OH 1-388 H Cl H CF₃ CH₃ OH 1-389 H Br H CF₃ CH₃ OH 1-390 F F H CF₃ CH₃ OH 1-391 F Cl H CF₃ CH₃ OH 1-392 F Br H CF₃ CH₃ OH 1-393 H Cl H CF₃ CH₃ NHCH₃ 1-394 H Cl H CF₃ CH₃ NHC₂H₅ 1-395 H Cl H CF₃ CH₃ NHCH₂CH═CH₂ 1-396 H Cl H CF₃ CH₃ NHCH₂C≡CH 1-397 H Cl H CF₃ CH₃ NHCH(CH₃)C≡CH 1-398 H Cl H CF₃ CH₃ NHSO₂CH₃ 1-399 H Cl H CF₃ CH₃ NHSO₂C₂H₅ 1-400 H Cl H CF₃ CH₃ NHSO₂CH₂Cl 1-401 H Cl H CF₃ CH₃ NHSO₂CF₃ 1-402 H Cl H CF₃ CH₃ N(CH₃)SO₂CH₃ 1-403 H Cl H CF₃ CH₃ N(CH₂C≡CH)SO₂CH₃ 1-404 H Cl H CF₃ CH₃ NHCOOCH₃ 1-405 H Cl H CF₃ CH₃ NHCOOC₂H₅ 1-406 H Cl H CF₃ CH₃ NHCOO^(n)C₃H₇ 1-407 H Cl H CF₃ CH₃ NHCOO^(i)C₃H₇ 1-408 H Cl H CF₃ CH₃ NHCOO^(n)C₄H₉ 1-409 H Cl H CF₃ CH₃ NHCOO^(n)C₅H₁₁ 1-410 H Cl H CF₃ CH₃ NHCH₂COOCH₃ 1-411 H Cl H CF₃ CH₃ NHCH₂COOC₂H₅ 1-412 H Cl H CF₃ CH₃ NHCH₂COO^(n)C₃H₇ 1-413 H Cl H CF₃ CH₃ NHCH₂COO^(n)C₄H₉ 1-414 H Cl H CF₃ CH₃ NHCH₂COO^(n)C₅H₁₁ 1-415 H Cl H CF₃ CH₃ NHCH₂COO^(i)C₃H₇ 1-416 H Cl H CF₃ CH₃ NHCH₂COO^(c)C₅H₉ 1-417 H Cl H CF₃ CH₃ NHCH₂COO^(c)C₆H₁₁ 1-418 F Cl H CF₃ CH₃ NHCH₂COO^(c)C₆H₁₁ 1-419 F Cl H CF₃ CH₃ NHCH(CH₃)COOCH₃ 1-420 F Cl H CF₃ CH₃ NHCH(CH₃)COOC₂H₅ 1-421 F Cl H CF₃ CH₃ NHCH(CH₃)COO^(n)C₃H₇ 1-422 F Cl H CF₃ CH₃ NHCH(CH₃)COO^(n)C₄H₉ 1-423 F Cl H CF₃ CH₃ NHCH(CH₃)COO^(n)C₅H₁₁ 1-424 F Cl H CF₃ CH₃ NHCH(CH₃)COO^(i)C₃H₇ 1-425 F Cl H CF₃ CH₃ NHCH(CH₃)COO^(c)C₅H₉ 1-426 F Cl H CF₃ CH₃ NHCH(CH₃)COO^(c)C₆H₁₁ 1-427 H Cl H CF₃ CH₃ OCH₃ 1-428 H Cl H CF₃ CH₃ OC₂H₅ 1-429 H Cl H CF₃ CH₃ O^(i)C₃H₇ 1-430 H Cl H CF₃ CH₃ O^(n)C₃H₇ 1-431 H Cl H CF₃ CH₃ OCH₂CH₂Cl 1-432 H Cl H CF₃ CH₃ OCF₂CF₂H 1-433 H Cl H CF₃ CH₃ O^(c)C₅H₉ 1-434 H Cl H CF₃ CH₃ O^(c)C₆H₁₁ 1-435 H Cl H CF₃ CH₃ OCH₂CH═CH₂ 1-436 H Cl H CF₃ CH₃ OCH₂CCl═CH₂ 1-437 H Cl H CF₃ CH₃ OCH₂CCl═CHCl 1-438 H Cl H CF₃ CH₃ OCH(CH₃)CH═CH₂ 1-439 H Cl H CF₃ CH₃ OCH₂C≡CH 1-440 H Cl H CF₃ CH₃ OCH(CH₃)C≡CH 1-441 H Cl H CF₃ CH₃ OCH₂C≡CBr 1-442 H Cl H CF₃ CH₃ OCH₂C≡CCl 1-443 H Cl H CF₃ CH₃ OCH₂C≡CCH₂Cl 1-444 H Cl H CF₃ CH₃ OCH₂CN 1-445 H Cl H CF₃ CH₃ OCH₂OCH₃ 1-446 H Cl H CF₃ CH₃ OCH₂OC₂H₅ 1-447 H Cl H CF₃ CH₃ OCH₂SCH₃ 1-448 H Cl H CF₃ CH₃ OCH₂COOCH₃ 1-449 H Cl H CF₃ CH₃ OCH₂COOC₂H₅ 1-450 H Cl H CF₃ CH₃ OCH₂COO^(n)C₃H₇ 1-451 H Cl H CF₃ CH₃ OCH₂COO^(n)C₄H₉ 1-452 H Cl H CF₃ CH₃ OCH₂COO^(n)C₅H₁₁ 1-453 H Cl H CF₃ CH₃ OCH₂COO^(i)C₃H₇ 1-454 H Cl H CF₃ CH₃ OCH₂COO^(c)C₅H₉ 1-455 H Cl H CF₃ CH₃ OCH₂COO^(c)C₆H₁₁ 1-456 H Cl H CF₃ CH₃ OCH(CH₃)COOCH₃ 1-457 H Cl H CF₃ CH₃ OCH(CH₃)COOC₂H₅ 1-458 H Cl H CF₃ CH₃ OCH(CH₃)COO^(n)C₃H₇ 1-459 H Cl H CF₃ CH₃ OCH(CH₃)COO^(n)C₄H₉ 1-460 H Cl H CF₃ CH₃ OCH(CH₃)COO^(n)C₅H₁₁ 1-461 H Cl H CF₃ CH₃ OCH(CH₃)COO^(i)C₃H₇ 1-462 H Cl H CF₃ CH₃ OCH(CH₃)COO^(c)C₅H₉ 1-463 H Cl H CF₃ CH₃ OCH(CH₃)COO^(c)C₆H₁₁ 1-464 H Cl H CF₃ CH₃ OCH₂CON(CH₃)₂ 1-465 H Cl H CF₃ CH₃ OCH₂CON(C₂H₅)₂ 1-466 H Cl H CF₃ CH₃ OCH₂CON(CH₃)C₂H₅ 1-467 H Cl H CF₃ CH₃ OCH(CH₃)CON(CH₃)₂ 1-468 H Cl H CF₃ CH₃ OCH(CH₃)CON(C₂H₅)₂ 1-469 H Cl H CF₃ CH₃ OCH(CH₃)CON(CH₃)C₂H₅ 1-470 H Cl H CF₃ CH₃ OCH₂COON(CH₃)₂ 1-471 H Cl H CF₃ CH₃ OCH₂COON(C₂H₅)₂ 1-472 H Cl H CF₃ CH₃ OCH(CH₃)COON(CH₃)₂ 1-473 H Cl H CF₃ CH₃ OCH(CH₃)COON(C₂H₅)₂ 1-474 F Cl H CF₃ CH₃ OCH₃ 1-475 F Cl H CF₃ CH₃ OC₂H₅ 1-476 F Cl H CF₃ CH₃ O^(i)C₃H₇ 1-477 F Cl H CF₃ CH₃ O^(n)C₃H₇ 1-478 F Cl H CF₃ CH₃ OCH₂CH₂Cl 1-479 F Cl H CF₃ CH₃ OCF₂CF₂H 1-480 F Cl H CF₃ CH₃ O^(c)C₅H₉ 1-481 F Cl H CF₃ CH₃ O^(c)C₆H₁₁ 1-482 F Cl H CF₃ CH₃ OCH₂CH═CH₂ 1-483 F Cl H CF₃ CH₃ OCH₂CCl═CH₂ 1-484 F Cl H CF₃ CH₃ OCH₂CCl═CHCl 1-485 F Cl H CF₃ CH₃ OCH(CH₃)CH═CH₂ 1-486 F Cl H CF₃ CH₃ OCH₂C≡CH 1-487 F Cl H CF₃ CH₃ OCH(CH₃)C≡CH 1-488 F Cl H CF₃ CH₃ OCH₂C≡CBr 1-489 F Cl H CF₃ CH₃ OCH₂C≡CCl 1-490 F Cl H CF₃ CH₃ OCH₂C≡CCH₂Cl 1-491 F Cl H CF₃ CH₃ OCH₂CN 1-492 F Cl H CF₃ CH₃ OCH₂OCH₃ 1-493 F Cl H CF₃ CH₃ OCH₂OC₂H₅ 1-494 F Cl H CF₃ CH₃ OCH₂SCH₃ 1-495 F Cl H CF₃ CH₃ OCH₂COOCH₃ 1-496 F Cl H CF₃ CH₃ OCH₂COOC₂H₅ 1-497 F Cl H CF₃ CH₃ OCH₂COO^(n)C₃H₇ 1-498 F Cl H CF₃ CH₃ OCH₂COO^(n)C₄H₉ 1-499 F Cl H CF₃ CH₃ OCH₂COO^(n)C₅H₁₁ 1-500 F Cl H CF₃ CH₃ OCH₂COO^(i)C₃H₇ 1-501 F Cl H CF₃ CH₃ OCH₂COO^(c)C₅H₉ 1-502 F Cl H CF₃ CH₃ OCH₂COO^(c)C₆H₁₁ 1-503 F Cl H CF₃ CH₃ OCH(CH₃)COOCH₃ 1-504 F Cl H CF₃ CH₃ OCH(CH₃)COOC₂H₅ 1-505 F Cl H CF₃ CH₃ OCH(CH₃)COO^(n)C₃H₇ 1-506 F Cl H CF₃ CH₃ OCH(CH₃)COO^(n)C₄H₉ 1-507 F Cl H CF₃ CH₃ OCH(CH₃)COO^(n)C₅H₁₁ 1-508 F Cl H CF₃ CH₃ OCH(CH₃)COO^(i)C₃H₇ 1-509 F Cl H CF₃ CH₃ OCH(CH₃)COO^(c)C₅H₉ 1-510 F Cl H CF₃ CH₃ OCH(CH₃)COO^(c)C₆H₁₁ 1-511 F Cl H CF₃ CH₃ OCH₂CON(CH₃)₂ 1-512 F Cl H CF₃ CH₃ OCH₂CON(C₂H₅)₂ 1-513 F Cl H CF₃ CH₃ OCH₂CON(CH₃)C₂H₅ 1-514 F Cl H CF₃ CH₃ OCH(CH₃)CON(CH₃)₂ 1-515 F Cl H CF₃ CH₃ OCH(CH₃)CON(C₂H₅)₂ 1-516 F Cl H CF₃ CH₃ OCH(CH₃)CON(CH₃)C₂H₅ 1-517 F Cl H CF₃ CH₃ OCH₂COON(CH₃)₂ 1-518 F Cl H CF₃ CH₃ OCH₂COON(C₂H₅)₂ 1-519 F Cl H CF₃ CH₃ OCH(CH₃)COON(CH₃)₂ 1-520 F Cl H CF₃ CH₃ OCH(CH₃)COON(C₂H₅)₂ 1-521 H F H CF₃ CH₃ SH 1-522 H Cl H CF₃ CH₃ SH 1-523 H Br H CF₃ CH₃ SH 1-524 F F H CF₃ CH₃ SH 1-525 F Cl H CF₃ CH₃ SH 1-526 F Br H CF₃ CH₃ SH 1-527 H Cl H CF₃ CH₃ SCH₃ 1-528 H Cl H CF₃ CH₃ SC₂H₅ 1-529 H Cl H CF₃ CH₃ S^(i)C₃H₇ 1-530 H Cl H CF₃ CH₃ SCH₂CH₂Cl 1-531 H Cl H CF₃ CH₃ S^(c)C₅H₉ 1-532 H Cl H CF₃ CH₃ S^(c)C₆H₁₁ 1-533 H Cl H CF₃ CH₃ SCH₂CH═CH₂ 1-534 H Cl H CF₃ CH₃ SCH₂CCl═CH₂ 1-535 H Cl H CF₃ CH₃ SCH₂CCl═CHCl 1-536 H Cl H CF₃ CH₃ SCH(CH₃)CH═CH₂ 1-537 H Cl H CF₃ CH₃ SCH₂C≡CH 1-538 H Cl H CF₃ CH₃ SCH(CH₃)C≡CH 1-539 H Cl H CF₃ CH₃ SCH₂COOCH₃ 1-540 H Cl H CF₃ CH₃ SCH₂COOC₂H₅ 1-541 H Cl H CF₃ CH₃ SCH₂COO^(n)C₃H₇ 1-542 H Cl H CF₃ CH₃ SCH₂COO^(n)C₄H₉ 1-543 H Cl H CF₃ CH₃ SCH₂COO^(n)C₅H₁₁ 1-544 H Cl H CF₃ CH₃ SCH₂COO^(i)C₃H₇ 1-545 H Cl H CF₃ CH₃ SCH₂COO^(c)C₅H₉ 1-546 H Cl H CF₃ CH₃ SCH₂COO^(c)C₆H₁₁ 1-547 H Cl H CF₃ CH₃ SCH(CH₃)COOCH₃ 1-548 H Cl H CF₃ CH₃ SCH(CH₃)COOC₂H₅ 1-549 H Cl H CF₃ CH₃ SCH(CH₃)COO^(n)C₃H₇ 1-550 H Cl H CF₃ CH₃ SCH(CH₃)COO^(n)C₄H₉ 1-551 H Cl H CF₃ CH₃ SCH(CH₃)COO^(n)C₅H₁₁ 1-552 H Cl H CF₃ CH₃ SCH(CH₃)COO^(i)C₃H₇ 1-553 H Cl H CF₃ CH₃ SCH(CH₃)COO^(c)C₅H₉ 1-554 H Cl H CF₃ CH₃ SCH(CH₃)COO^(c)C₆H₁₁ 1-555 H Cl H CF₃ CH₃ SCH₂CON(CH₃)₂ 1-556 H Cl H CF₃ CH₃ SCH₂CON(C₂H₅)₂ 1-557 H Cl H CF₃ CH₃ SCH₂CON(tetramethylene) 1-558 H Cl H CF₃ CH₃ SCH₂CON(pentamethylene) 1-559 H Cl H CF₃ CH₃ SCH₂CON(ethyleneoxyethylene) 1-560 H Cl H CF₃ CH₃ SCH(CH₃)CON(CH₃)₂ 1-561 H Cl H CF₃ CH₃ SCH(CH₃)CON(C₂H₅)₂ 1-562 H Cl H CF₃ CH₃ SCH(CH₃)CON(tetramethylene) 1-563 H Cl H CF₃ CH₃ SCH(CH₃)CON(pentamethylene) 1-564 F Cl H CF₃ CH₃ SCH₃ 1-565 F Cl H CF₃ CH₃ SC₂H₅ 1-566 F Cl H CF₃ CH₃ S^(i)C₃H₇ 1-567 F Cl H CF₃ CH₃ SCH₂CH₂Cl 1-568 F Cl H CF₃ CH₃ S^(c)C₅H₉ 1-569 F Cl H CF₃ CH₃ S^(c)C₆H₁₁ 1-570 F Cl H CF₃ CH₃ SCH₂CH═CH₂ 1-571 F Cl H CF₃ CH₃ SCH₂CCl═CH₂ 1-572 F Cl H CF₃ CH₃ SCH₂CCl═CHCl 1-573 F Cl H CF₃ CH₃ SCH(CH₃)CH═CH₂ 1-574 F Cl H CF₃ CH₃ SCH₂C≡CH 1-575 F Cl H CF₃ CH₃ SCH(CH₃)C≡CH 1-576 F Cl H CF₃ CH₃ SCH₂COOCH₃ 1-577 F Cl H CF₃ CH₃ SCH₂COOC₂H₅ 1-578 F Cl H CF₃ CH₃ SCH₂COO^(n)C₃H₇ 1-579 F Cl H CF₃ CH₃ SCH₂COO^(n)C₄H₉ 1-580 F Cl H CF₃ CH₃ SCH₂COO^(n)C₅H₁₁ 1-581 F Cl H CF₃ CH₃ SCH₂COO^(i)C₃H₇ 1-582 F Cl H CF₃ CH₃ SCH₂COO^(c)C₅H₉ 1-583 F Cl H CF₃ CH₃ SCH₂COO^(c)C₆H₁₁ 1-584 F Cl H CF₃ CH₃ SCH(CH₃)COOCH₃ 1-585 F Cl H CF₃ CH₃ SCH(CH₃)COOC₂H₅ 1-586 F Cl H CF₃ CH₃ SCH(CH₃)COO^(n)C₃H₇ 1-587 F Cl H CF₃ CH₃ SCH(CH₃)COO^(n)C₄H₉ 1-588 F Cl H CF₃ CH₃ SCH(CH₃)COO^(n)C₅H₁₁ 1-589 F Cl H CF₃ CH₃ SCH(CH₃)COO^(i)C₃H₇ 1-590 F Cl H CF₃ CH₃ SCH(CH₃)COO^(c)C₅H₉ 1-591 F Cl H CF₃ CH₃ SCH(CH₃)COO^(c)C₆H₁₁ 1-592 F Cl H CF₃ CH₃ SCH₂CON(CH₃)₂ 1-593 F Cl H CF₃ CH₃ SCH₂CON(C₂H₅)₂ 1-594 F Cl H CF₃ CH₃ SCH₂CON(tetramethylene) 1-595 F Cl H CF₃ CH₃ SCH₂CON(pentamethylene) 1-596 F Cl H CF₃ CH₃ SCH₂CON(ethyleneoxyethylene) 1-597 F Cl H CF₃ CH₃ SCH(CH₃)CON(CH₃)₂ 1-598 F Cl H CF₃ CH₃ SCH(CH₃)CON(C₂H₅)₂ 1-599 F Cl H CF₃ CH₃ SCH(CH₃)CON(tetramethylene) 1-600 F Cl H CF₃ CH₃ SCH(CH₃)CON(pentamethylene) 1-601 H F H CF₃ CH₃ SO₂Cl 1-602 H Cl H CF₃ CH₃ SO₂Cl 1-603 H Br H CF₃ CH₃ SO₂Cl 1-604 F F H CF₃ CH₃ SO₂Cl 1-605 F Cl H CF₃ CH₃ SO₂Cl 1-606 F Br H CF₃ CH₃ SO₂Cl 1-607 H Cl H CF₃ CH₃ SO₂OCH₃ 1-608 H Cl H CF₃ CH₃ SO₂OC₂H₅ 1-609 H Cl H CF₃ CH₃ SO₂O^(i)C₃H₇ 1-610 H Cl H CF₃ CH₃ SO₂OCH₂CH═CH₂ 1-611 F Cl H CF₃ CH₃ SO₂OCH₃ 1-612 F Cl H CF₃ CH₃ SO₂OC₂H₅ 1-613 F Cl H CF₃ CH₃ SO₂O^(i)C₃H₇ 1-614 F Cl H CF₃ CH₃ SO₂OCH₂CH═CH₂ 1-615 H Cl H CF₃ CH₃ SO₂N(CH₃)₂ 1-616 H Cl H CF₃ CH₃ SO₂N(C₂H₅)₂ 1-617 F Cl H CF₃ CH₃ SO₂N(CH₃)₂ 1-618 F Cl H CF₃ CH₃ SO₂N(C₂H₅)₂ 1-619 H Cl H CF₃ CH₃ COOH 1-620 H Cl H CF₃ CH₃ COOCH₃ 1-621 H Cl H CF₃ CH₃ COOC₂H₅ 1-622 H Cl H CF₃ CH₃ COO^(n)C₃H₇ 1-623 H Cl H CF₃ CH₃ COO^(n)C₄H₉ 1-624 H Cl H CF₃ CH₃ COO^(n)C₅H₁₁ 1-625 H Cl H CF₃ CH₃ COO^(i)C₃H₇ 1-626 H Cl H CF₃ CH₃ COOCH₂CH₂Cl 1-627 H Cl H CF₃ CH₃ COOCH₂CH₂Br 1-628 H Cl H CF₃ CH₃ CON(CH₃)₂ 1-629 H Cl H CF₃ CH₃ CONHCH₃ 1-630 H Cl H CF₃ CH₃ CON(C₂H₅)₂ 1-631 H Cl H CF₃ CH₃ CONHC₂H₅ 1-632 H Cl H CF₃ CH₃ COCH₃ 1-633 H Cl H CF₃ CH₃ COC₂H₅ 1-634 H Cl H CF₃ CH₃ COCH₂Cl 1-635 H Cl H CF₃ CH₃ CHO 1-636 H Cl H CF₃ CH₃ CH═CHCOOCH₃ 1-637 H Cl H CF₃ CH₃ CH═CHCOOC₂H₅ 1-638 H Cl H CF₃ CH₃ CH₂CH₂COOCH₃ 1-639 H Cl H CF₃ CH₃ CH₂CH₂COOC₂H₅ 1-640 F Cl H CF₃ CH₃ COOH 1-641 F Cl H CF₃ CH₃ COOCH₃ 1-642 F Cl H CF₃ CH₃ COOC₂H₅ 1-643 F Cl H CF₃ CH₃ COO^(n)C₃H₇ 1-644 F Cl H CF₃ CH₃ COO^(n)C₄H₉ 1-645 F Cl H CF₃ CH₃ COO^(n)C₅H₁₁ 1-646 F Cl H CF₃ CH₃ COO^(i)C₃H₇ 1-647 F Cl H CF₃ CH₃ COOCH₂CH₂Cl 1-648 F Cl H CF₃ CH₃ COOCH₂CH₂Br 1-649 F Cl H CF₃ CH₃ CON(CH₃)₂ 1-650 F Cl H CF₃ CH₃ CONHCH₃ 1-651 F Cl H CF₃ CH₃ CON(C₂H₅)₂ 1-652 F Cl H CF₃ CH₃ CONHC₂H₅ 1-653 F Cl H CF₃ CH₃ COCH₃ 1-654 F Cl H CF₃ CH₃ COC₂H₅ 1-655 F Cl H CF₃ CH₃ COCH₂Cl 1-656 F Cl H CF₃ CH₃ CHO 1-657 F Cl H CF₃ CH₃ CH═CHCOOCH₃ 1-658 F Cl H CF₃ CH₃ CH═CHCOOC₂H₅ 1-659 F Cl H CF₃ CH₃ CH₂CH₂COOCH₃ 1-660 F Cl H CF₂Cl CH₃ CH₂CH₂COOC₂H₅ 1-661 Cl Cl H CF₂Cl H H 1-662 H F H CF₂Cl H NO₂ 1-663 H Cl H CF₂Cl H NO₂ 1-664 H Br H CF₂Cl H NO₂ 1-665 F F H CF₂Cl H NO₂ 1-666 F Cl H CF₂Cl H NO₂ 1-667 F Br H CF₂Cl H NO₂ 1-668 H F H CF₂Cl H NH₂ 1-669 H Cl H CF₂Cl H NH₂ 1-670 H Br H CF₂Cl H NH₂ 1-671 F F H CF₂Cl H NH₂ 1-672 F Cl H CF₂Cl H NH₂ 1-673 F Br H CF₂Cl H NH₂ 1-674 H F H CF₂Cl H OH 1-675 H Cl H CF₂Cl H OH 1-676 H Br H CF₂Cl H OH 1-677 F F H CF₂Cl H OH 1-678 F Cl H CF₂Cl H OH 1-679 F Br H CF₂Cl H OH 1-680 H Cl H CF₂Cl H NHCH₃ 1-681 H Cl H CF₂Cl H NHC₂H₅ 1-682 H Cl H CF₂Cl H NHCH₂CH═CH₂ 1-683 H Cl H CF₂Cl H NHCH₂C≡CH 1-684 H Cl H CF₂Cl H NHCH(CH₃)C≡CH 1-685 H Cl H CF₂Cl H NHSO₂CH₃ 1-686 H Cl H CF₂Cl H NHSO₂C₂H₅ 1-687 H Cl H CF₂Cl H NHSO₂CH₂Cl 1-688 H Cl H CF₂Cl H NHSO₂CF₃ 1-689 H Cl H CF₂Cl H N(CH₃)SO₂CH₃ 1-690 H Cl H CF₂Cl H N(CH₂C≡CH)SO₂CH₃ 1-691 H Cl H CF₂Cl H NHCOOCH₃ 1-692 H Cl H CF₂Cl H NHCOOC₂H₅ 1-693 H Cl H CF₂Cl H NHCOO^(n)C₃H₇ 1-694 H Cl H CF₂Cl H NHCOO^(i)C₃H₇ 1-695 H Cl H CF₂Cl H NHCOO^(n)C₄H₉ 1-696 H Cl H CF₂Cl H NHCOO^(n)C₅H₁₁ 1-697 H Cl H CF₂Cl H NHCH₂COOCH₃ 1-698 H Cl H CF₂Cl H NHCH₂COOC₂H₅ 1-699 H Cl H CF₂Cl H NHCH₂COO^(n)C₃H₇ 1-700 H Cl H CF₂Cl H NHCH₂COO^(n)C₄H₉ 1-701 H Cl H CF₂Cl H NHCH₂COO^(n)C₅H₁₁ 1-702 H Cl H CF₂Cl H NHCH₂COO^(i)C₃H₇ 1-703 H Cl H CF₂Cl H NHCH₂COO^(c)C₅H₉ 1-704 H Cl H CF₂Cl H NHCH₂COO^(c)C₆H₁₁ 1-705 H Cl H CF₂Cl H NHCH(CH₃)COOCH₃ 1-706 H Cl H CF₂Cl H NHCH(CH₃)COOC₂H₅ 1-707 H Cl H CF₂Cl H NHCH(CH₃)COO^(n)C₃H₇ 1-708 H Cl H CF₂Cl H NHCH(CH₃)COO^(n)C₄H₉ 1-709 H Cl H CF₂Cl H NHCH(CH₃)COO^(n)C₅H₁₁ 1-710 H Cl H CF₂Cl H NHCH(CH₃)COO^(i)C₃H₇ 1-711 H Cl H CF₂Cl H NHCH(CH₃)COO^(c)C₅H₉ 1-712 H Cl H CF₂Cl H NHCH(CH₃)COO^(c)C₆H₁₁ 1-713 F Cl H CF₂Cl H NHCH₃ 1-714 F Cl H CF₂Cl H NHC₂H₅ 1-715 F Cl H CF₂Cl H NHCH₂CH═CH₂ 1-716 F Cl H CF₂Cl H NHCH₂C≡CH 1-717 F Cl H CF₂Cl H NHCH(CH₃)C≡CH 1-718 F Cl H CF₂Cl H NHSO₂CH₃ 1-719 F Cl H CF₂Cl H NHSO₂C₂H₅ 1-720 F Cl H CF₂Cl H NHSO₂CH₂Cl 1-721 F Cl H CF₂Cl H NHSO₂CF₃ 1-722 F Cl H CF₂Cl H N(CH₃)SO₂CH₃ 1-723 F Cl H CF₂Cl H N(CH₂C≡CH)SO₂CH₃ 1-724 F Cl H CF₂Cl H NHCOOCH₃ 1-725 F Cl H CF₂Cl H NHCOOC₂H₅ 1-726 F Cl H CF₂Cl H NHCOO^(n)C₃H₇ 1-727 F Cl H CF₂Cl H NHCOO^(i)C₃H₇ 1-728 F Cl H CF₂Cl H NHCOO^(n)C₄H₉ 1-729 F Cl H CF₂Cl H NHCOO^(n)C₅H₁₁ 1-730 F Cl H CF₂Cl H NHCH₂COOCH₃ 1-731 F Cl H CF₂Cl H NHCH₂COOC₂H₅ 1-732 F Cl H CF₂Cl H NHCH₂COO^(n)C₃H₇ 1-733 F Cl H CF₂Cl H NHCH₂COO^(n)C₄H₉ 1-734 F Cl H CF₂Cl H NHCH_(2COO) ^(n)C₅H₁₁ 1-735 F Cl H CF₂Cl H NHCH₂COO^(i)C₃H₇ 1-736 F Cl H CF₂Cl H NHCH₂COO^(c)C₅H₉ 1-737 F Cl H CF₂Cl H NH₂CH₂COO^(c)C₆H₁₁ 1-738 F Cl H CF₂Cl H NHCH(CH₃)COOCH₃ 1-739 F Cl H CF₂Cl H NHCH(CH₃)COOC₂H₅ 1-740 F Cl H CF₂Cl H NHCH(CH₃)COO^(n)C₃H₇ 1-741 F Cl H CF₂Cl H NHCH(CH₃)COO^(n)C₄H₉ 1-742 F Cl H CF₂Cl H NHCH(CH₃)COO^(n)C₅H₁₁ 1-743 F Cl H CF₂Cl H NHCH(CH₃)COO^(i)C₃H₇ 1-744 F Cl H CF₂Cl H NHCH(CH₃)COO^(c)C₅H₉ 1-745 F Cl H CF₂Cl H NHCH(CH₃)COO^(c)C₆H₁₁ 1-746 H Cl H CF₂Cl H OCH₃ 1-747 H Cl H CF₂Cl H OC₂H₅ 1-748 H Cl H CF₂Cl H O^(i)C₃H₇ 1-749 H Cl H CF₂Cl H O^(n)C₃H₇ 1-750 H Cl H CF₂Cl H OCH₂CH₂Cl 1-751 H Cl H CF₂Cl H OCF₂CF₂H 1-752 H Cl H CF₂Cl H O^(c)C₅H₉ 1-753 H Cl H CF₂Cl H O^(c)C₆H₁₁ 1-754 H Cl H CF₂Cl H OCH₂CH═CH₂ 1-755 H Cl H CF₂Cl H OCH₂CCl═CH₂ 1-756 H Cl H CF₂Cl H OCH₂CCl═CHCl 1-757 H Cl H CF₂Cl H OCH(CH₃)CH═CH₂ 1-758 H Cl H CF₂Cl H OCH₂C≡CH 1-759 H Cl H CF₂Cl H OCH(CH₃)C≡CH 1-760 H Cl H CF₂Cl H OCH₂C≡CBr 1-761 H Cl H CF₂Cl H OCH₂C≡CCl 1-762 H Cl H CF₂Cl H OCH₂C≡CCH₂Cl 1-763 H Cl H CF₂Cl H OCH₂CN 1-764 H Cl H CF₂Cl H OCH₂OCH₃ 1-765 H Cl H CF₂Cl H OCH₂OC₂H₅ 1-766 H Cl H CF₂Cl H OCH₂SCH₃ 1-767 H Cl H CF₂Cl H OCH₂COOCH₃ 1-768 H Cl H CF₂Cl H OCH₂COOC₂H₅ 1-769 H Cl H CF₂Cl H OCH₂COO^(n)C₃H₇ 1-770 H Cl H CF₂Cl H OCH₂COO^(n)C₄H₉ 1-771 H Cl H CF₂Cl H OCH₂COO^(n)C₅H₁₁ 1-772 H Cl H CF₂Cl H OCH₂COO^(i)C₃H₇ 1-773 H Cl H CF₂Cl H OCH₂COO^(c)C₅H₉ 1-774 H Cl H CF₂Cl H OCH₂COO^(c)C₆H₁₁ 1-775 H Cl H CF₂Cl H OCH(CH₃)COOCH₃ 1-776 H Cl H CF₂Cl H OCH(CH₃)COOC₂H₅ 1-777 H Cl H CF₂Cl H OCH(CH₃)COO^(n)C₃H₇ 1-778 H Cl H CF₂Cl H OCH(CH₃)COO^(n)C₄H₉ 1-779 H Cl H CF₂Cl H OCH(CH₃)COO^(n)C₅H₁₁ 1-780 H Cl H CF₂Cl H OCH(CH₃)COO^(i)C₃H₇ 1-781 H Cl H CF₂Cl H OCH(CH₃)COO^(c)C₅H₉ 1-782 H Cl H CF₂Cl H OCH(CH₃)COO^(c)C₆H₁₁ 1-783 H Cl H CF₂Cl H OCH₂CON(CH₃)₂ 1-784 H Cl H CF₂Cl H OCH₂CON(C₂H₅)₂ 1-785 H Cl H CF₂Cl H OCH₂CON(CH₃)C₂H₅ 1-786 H Cl H CF₂Cl H OCH(CH₃)CON(CH₃)₂ 1-787 H Cl H CF₂Cl H OCH(CH₃)CON(C₂H₅)₂ 1-788 H Cl H CF₂Cl H OCH(CH₃)CON(CH₃)C₂H₅ 1-789 H Cl H CF₂Cl H OCH₂COON(CH₃)₂ 1-790 H Cl H CF₂Cl H OCH₂COON(C₂H₅)₂ 1-791 H Cl H CF₂Cl H OCH(CH₃)COON(CH₃)₂ 1-792 H Cl H CF₂Cl H OCH(CH₃)COON(C₂H₅)₂ 1-793 F Cl H CF₂Cl H OCH₃ 1-794 F Cl H CF₂Cl H OC₂H₅ 1-795 F Cl H CF₂Cl H O^(i)C₃H₇ 1-796 F Cl H CF₂Cl H O^(n)C₃H₇ 1-797 F Cl H CF₂Cl H OCH₂CH₂Cl 1-798 F Cl H CF₂Cl H OCF₂CF₂H 1-799 F Cl H CF₂Cl H O^(c)C₅H₉ 1-800 F Cl H CF₂Cl H O^(c)C₆H₁₁ 1-801 F Cl H CF₂Cl H OCH₂CH═CH₂ 1-802 F Cl H CF₂Cl H OCH₂CCl═CH₂ 1-803 F Cl H CF₂Cl H OCH₂CCl═CHCl 1-804 F Cl H CF₂Cl H OCH(CH₃)CH═CH₂ 1-805 F Cl H CF₂Cl H OCH₂C≡CH 1-806 F Cl H CF₂Cl H OCH(CH₃)C≡CH 1-807 F Cl H CF₂Cl H OCH₂C≡CBr 1-808 F Cl H CF₂Cl H OCH₂C≡CCl 1-809 F Cl H CF₂Cl H OCH₂C≡CCH₂Cl 1-810 F Cl H CF₂Cl H OCH₂CN 1-811 F Cl H CF₂Cl H OCH₂OCH₃ 1-812 F Cl H CF₂Cl H OCH₂OC₂H₅ 1-813 F Cl H CF₂Cl H OCH₂SCH₃ 1-814 F Cl H CF₂Cl H OCH₂COOCH₃ 1-815 F Cl H CF₂Cl H OCH₂COOC₂H₅ 1-816 F Cl H CF₂Cl H OCH₂COO^(n)C₃H₇ 1-817 F Cl H CF₂Cl H OCH₂COO^(n)C₄H₉ 1-818 F Cl H CF₂Cl H OCH₂COO^(n)C₅H₁₁ 1-819 F Cl H CF₂Cl H OCH₂COO^(i)C₃H₇ 1-820 F Cl H CF₂Cl H OCH₂COO^(c)C₅H₉ 1-821 F Cl H CF₂Cl H OCH₂COO^(c)C₆H₁₁ 1-822 F Cl H CF₂Cl H OCH(CH₃)COOCH₃ 1-823 F Cl H CF₂Cl H OCH(CH₃)COOC₂H₅ 1-824 F Cl H CF₂Cl H OCH(CH₃)COO^(n)C₃H₇ 1-825 F Cl H CF₂Cl H OCH(CH₃)COO^(n)C₄H₉ 1-826 F Cl H CF₂Cl H OCH(CH₃)COO^(n)C₅H₁₁ 1-827 F Cl H CF₂Cl H OCH(CH₃)COO^(i)C₃H₇ 1-828 F Cl H CF₂Cl H OCH(CH₃)COO^(c)C₅H₉ 1-829 F Cl H CF₂Cl H OCH(CH₃)COO^(c)C₆H₁₁ 1-830 F Cl H CF₂Cl H OCH₂CON(CH₃)₂ 1-831 F Cl H CF₂Cl H OCH₂CON(C₂H₅)₂ 1-832 F Cl H CF₂Cl H OCH₂CON(CH₃)C₂H₅ 1-833 F Cl H CF₂Cl H OCH(CH₃)CON(CH₃)₂ 1-834 F Cl H CF₂Cl H OCH(CH₃)CON(C₂H₅)₂ 1-835 F Cl H CF₂Cl H OCH(CH₃)CON(CH₃)C₂H₅ 1-836 F Cl H CF₂Cl H OCH₂COON(CH₃)₂ 1-837 F Cl H CF₂Cl H OCH₂COON(C₂H₅)₂ 1-838 F Cl H CF₂Cl H OCH(CH₃)COON(CH₃)₂ 1-839 F Cl H CF₂Cl H OCH(CH₃)COON(C₂H₅)₂ 1-840 H F H CF₂Cl H SH 1-841 H Cl H CF₂Cl H SH 1-842 H Br H CF₂Cl H SH 1-843 F F H CF₂Cl H SH 1-844 F Cl H CF₂Cl H SH 1-845 F Br H CF₂Cl H SH 1-846 H Cl H CF₂Cl H SCH₃ 1-847 H Cl H CF₂Cl H SC₂H₅ 1-848 H Cl H CF₂Cl H S^(i)C₃H₇ 1-849 H Cl H CF₂Cl H SCH₂CH₂Cl 1-850 H Cl H CF₂Cl H S^(c)C₅H₉ 1-851 H Cl H CF₂Cl H S^(c)C₆H₁₁ 1-852 H Cl H CF₂Cl H SCH₂CH═CH₂ 1-853 H Cl H CF₂Cl H SCH₂CCl═CH₂ 1-854 H Cl H CF₂Cl H SCH₂CCl═CHCl 1-855 H Cl H CF₂Cl H SCH(CH₃)CH═CH₂ 1-856 H Cl H CF₂Cl H SCH₂C≡CH 1-857 H Cl H CF₂Cl H SCH(CH₃)C≡CH 1-858 H Cl H CF₂Cl H SCH₂COOCH₃ 1-859 H Cl H CF₂Cl H SCH₂COOC₂H₅ 1-860 H Cl H CF₂Cl H SCH₂COO^(n)C₃H₇ 1-861 H Cl H CF₂Cl H SCH₂COO^(n)C₄H₉ 1-862 H Cl H CF₂Cl H SCH₂COO^(n)C₅H₁₁ 1-863 H Cl H CF₂Cl H SCH₂COO^(i)C₃H₇ 1-864 H Cl H CF₂Cl H SCH₂COO^(c)C₅H₉ 1-865 H Cl H CF₂Cl H SCH₂COO^(c)C₆H₁₁ 1-866 H Cl H CF₂Cl H SCH(CH₃)COOCH₃ 1-867 H Cl H CF₂Cl H SCH(CH₃)COOC₂H₅ 1-868 H Cl H CF₂Cl H SCH(CH₃)COO^(n)C₃H₇ 1-869 H Cl H CF₂Cl H SCH(CH₃)COO^(n)C₄H₉ 1-870 H Cl H CF₂Cl H SCH(CH₃)COO^(n)C₅H₁₁ 1-871 H Cl H CF₂Cl H SCH(CH₃)COO^(i)C₃H₇ 1-872 H Cl H CF₂Cl H SCH(CH₃)COO^(c)C₅H₉ 1-873 H Cl H CF₂Cl H SCH(CH₃)COO^(c)C₆H₁₁ 1-874 H Cl H CF₂Cl H SCH₂CON(CH₃)₂ 1-875 H Cl H CF₂Cl H SCH₂CON(C₂H₅)₂ 1-876 H Cl H CF₂Cl H SCH₂CON(tetramethylene) 1-877 H Cl H CF₂Cl H SCH₂CON(pentamethylene) 1-878 H Cl H CF₂Cl H SCH₂CON(ethyleneoxyethylene) 1-879 H Cl H CF₂Cl H SCH(CH₃)CON(CH₃)₂ 1-880 H Cl H CF₂Cl H SCH(CH₃)CON(C₂H₅)₂ 1-881 H Cl H CF₂Cl H SCH(CH₃)CON(tetramethylene) 1-882 H Cl H CF₂Cl H SCH(CH₃)CON(pentamethylene) 1-883 F Cl H CF₂Cl H SCH₃ 1-884 F Cl H CF₂Cl H SC₂H₅ 1-885 F Cl H CF₂Cl H S^(i)C₃H₇ 1-886 F Cl H CF₂Cl H SCH₂CH₂Cl 1-887 F Cl H CF₂Cl H S^(c)C₅H₉ 1-888 F Cl H CF₂Cl H S^(c)C₆H₁₁ 1-889 F Cl H CF₂Cl H SCH₂CH═CH₂ 1-890 F Cl H CF₂Cl H SCH₂CCl═CH₂ 1-891 F Cl H CF₂Cl H SCH₂CCl═CHCl 1-892 F Cl H CF₂Cl H SCH(CH₃)CH═CH₂ 1-893 F Cl H CF₂Cl H SCH₂C≡CH 1-894 F Cl H CF₂Cl H SCH(CH₃)C≡CH 1-895 F Cl H CF₂Cl H SCH₂COOCH₃ 1-896 F Cl H CF₂Cl H SCH₂COOC₂H₅ 1-897 F Cl H CF₂Cl H SCH₂COO^(n)C₃H₇ 1-898 F Cl H CF₂Cl H SCH₂COO^(n)C₄H₉ 1-899 F Cl H CF₂Cl H SCH₂COO^(n)C₅H₁₁ 1-900 F Cl H CF₂Cl H SCH₂COO^(i)C₃H₇ 1-901 F Cl H CF₂Cl H SCH₂COO^(c)C₅H₉ 1-902 F Cl H CF₂Cl H SCH₂COO^(c)C₆H₁₁ 1-903 F Cl H CF₂Cl H SCH(CH₃)COOCH₃ 1-904 F Cl H CF₂Cl H SCH(CH₃)COOC₂H₅ 1-905 F Cl H CF₂Cl H SCH(CH₃)COO^(n)C₃H₇ 1-906 F Cl H CF₂Cl H SCH(CH₃)COO^(n)C₄H₉ 1-907 F Cl H CF₂Cl H SCH(CH₃)COO^(n)C₅H₁₁ 1-908 F Cl H CF₂Cl H SCH(CH₃)COO^(i)C₃H₇ 1-909 F Cl H CF₂Cl H SCH(CH₃)COO^(c)C₅H₉ 1-910 F Cl H CF₂Cl H SCH(CH₃)COO^(c)C₆H₁₁ 1-911 F Cl H CF₂Cl H SCH₂CON(CH₃)₂ 1-912 F Cl H CF₂Cl H SCH₂CON(C₂H₅)₂ 1-913 F Cl H CF₂Cl H SCH₂CON(tetramethylene) 1-914 F Cl H CF₂Cl H SCH₂CON(pentamethylene) 1-915 F Cl H CF₂Cl H SCH₂CON(ethyleneoxyethylene) 1-916 F Cl H CF₂Cl H SCH(CH₃)CON(CH₃)₂ 1-917 F Cl H CF₂Cl H SCH(CH₃)CON(C₂H₅)₂ 1-918 F Cl H CF₂Cl H SCH(CH₃)CON(tetramethylene) 1-919 F Cl H CF₂Cl H SCH(CH₃)CON(pentamethylene) 1-920 H F H CF₂Cl H SO₂Cl 1-921 H Cl H CF₂Cl H SO₂Cl 1-922 H Br H CF₂Cl H SO₂Cl 1-923 F F H CF₂Cl H SO₂Cl 1-924 F Cl H CF₂Cl H SO₂Cl 1-925 F Br H CF₂Cl H SO₂Cl 1-926 H Cl H CF₂Cl H SO₂OCH₃ 1-927 H Cl H CF₂Cl H SO₂OC₂H₅ 1-928 H Cl H CF₂Cl H SO₂O^(i)C₃H₇ 1-929 H Cl H CF₂Cl H SO₂OCH₂CH═CH₂ 1-930 F Cl H CF₂Cl H SO₂OCH₃ 1-931 F Cl H CF₂Cl H SO₂OC₂H₅ 1-932 F Cl H CF₂Cl H SO₂O^(i)C₃H₇ 1-933 F Cl H CF₂Cl H SO₂OCH₂CH═CH₂ 1-934 H Cl H CF₂Cl H SO₂N(CH₃)₂ 1-935 H Cl H CF₂Cl H SO₂N(C₂H₅)₂ 1-936 F Cl H CF₂Cl H SO₂N(CH₃)₂ 1-937 F Cl H CF₂Cl H SO₂N(C₂H₅)₂ 1-938 H Cl H CF₂Cl H COOH 1-939 H Cl H CF₂Cl H COOCH₃ 1-940 H Cl H CF₂Cl H COOC₂H₅ 1-941 H Cl H CF₂Cl H COO^(n)C₃H₇ 1-942 H Cl H CF₂Cl H COO^(n)C₄H₉ 1-943 H Cl H CF₂Cl H COO^(n)C₅H₁₁ 1-944 H Cl H CF₂Cl H COO^(i)C₃H₇ 1-945 H Cl H CF₂Cl H COOCH₂CH₂Cl 1-946 H Cl H CF₂Cl H COOCH₂CH₂Br 1-947 H Cl H CF₂Cl H CON(CH₃)₂ 1-948 H Cl H CF₂Cl H CONHCH₃ 1-949 H Cl H CF₂Cl H CON(C₂H₅)₂ 1-950 H Cl H CF₂Cl H CONHC₂H₅ 1-951 H Cl H CF₂Cl H COCH₃ 1-952 H Cl H CF₂Cl H COC₂H₅ 1-953 H Cl H CF₂Cl H COCH₂Cl 1-954 H Cl H CF₂Cl H CHO 1-955 H Cl H CF₂Cl H CH═CHCOOCH₃ 1-956 H Cl H CF₂Cl H CH═CHCOOC₂H₅ 1-957 H Cl H CF₂Cl H CH₂CH₂COOCH₃ 1-958 H Cl H CF₂Cl H CH₂CH₂COOC₂H₅ 1-959 F Cl H CF₂Cl H COOH 1-960 F Cl H CF₂Cl H COOCH₃ 1-961 F Cl H CF₂Cl H COOC₂H₅ 1-962 F Cl H CF₂Cl H COO^(n)C₃H₇ 1-963 F Cl H CF₂Cl H COO^(n)C₄H₉ 1-964 F Cl H CF₂Cl H COO^(n)C₅H₁₁ 1-965 F Cl H CF₂Cl H COO^(i)C₃H₇ 1-966 F Cl H CF₂Cl H COOCH₂CH₂Cl 1-967 F Cl H CF₂Cl H COOCH₂CH₂Br 1-968 F Cl H CF₂Cl H CON(CH₃)₂ 1-969 F Cl H CF₂Cl H CONHCH₃ 1-970 F Cl H CF₂Cl H CON(C₂H₅)₂ 1-971 F Cl H CF₂Cl H CONHC₂H₅ 1-972 F Cl H CF₂Cl H COCH₃ 1-973 F Cl H CF₂Cl H COC₂H₅ 1-974 F Cl H CF₂Cl H COCH₂Cl 1-975 F Cl H CF₂Cl H CHO 1-976 F Cl H CF₂Cl H CH═CHCOOCH₃ 1-977 F Cl H CF₂Cl H CH═CHCOOC₂H₅ 1-978 F Cl H CF₂Cl H CH₂CH₂COOCH₃ 1-979 F Cl H CF₂Cl H CH₂CH₂COOC₂H₅ 1-980 H F H CF₃ H NO₂ 1-981 H Cl H CF₃ H NO₂ 1-982 H Br H CF₃ H NO₂ 1-983 F F H CF₃ H NO₂ 1-984 F Cl H CF₃ H NO₂ 1-985 F Br H CF₃ H NO₂ 1-986 H F H CF₃ H NH₂ 1-987 H Cl H CF₃ H NH₂ 1-988 H Br H CF₃ H NH₂ 1-989 F F H CF₃ H NH₂ 1-990 F Cl H CF₃ H NH₂ 1-991 H Cl H CF₃ H NHCH(CH₃)COOCH₃ 1-992 H Cl H CF₃ H NHCH(CH₃)COOC₂H₅ 1-993 H Cl H CF₃ H NHCH(CH₃)COO^(n)C₃H₇ 1-994 H Cl H CF₃ H NHCH(CH₃)COO^(n)C₄H₉ 1-995 H Cl H CF₃ H NHCH(CH₃)COO^(n)C₅H₁₁ 1-996 H Cl H CF₃ H NHCH(CH₃)COO^(i)C₃H₇ 1-997 H Cl H CF₃ H NHCH(CH₃)COO^(c)C₅H₉ 1-998 H Cl H CF₃ H NHCH(CH₃)COO^(c)C₆H₁₁ 1-999 F Cl H CF₃ H NHCH₃ 1-1000 F Cl H CF₃ H NHC₂H₅ 1-1001 F Cl H CF₃ H NHCH₂CH═CH₂ 1-1002 F Cl H CF₃ H NHCH₂C≡CH 1-1003 F Cl H CF₃ H NHCH(CH₃)C≡CH 1-1004 F Cl H CF₃ H NHSO₂CH₃ 1-1005 F Cl H CF₃ H NHSO₂C₂H₅ 1-1006 F Cl H CF₃ H NHSO₂CH₂Cl 1-1007 F Cl H CF₃ H NHSO₂CF₃ 1-1008 F Cl H CF₃ H N(CH₃)SO₂CH₃ 1-1009 F Cl H CF₃ H N(CH₂C≡CH)SO₂CH₃ 1-1010 F Cl H CF₃ H NHCOOCH₃ 1-1011 F Cl H CF₃ H NHCOOC₂H₅ 1-1012 F Cl H CF₃ H NHCOO^(n)C₃H₇ 1-1013 F Cl H CF₃ H NHCOO^(i)C₃H₇ 1-1014 F Cl H CF₃ H NHCOO^(n)C₄H₉ 1-1015 F Cl H CF₃ H NHCOO^(n)C₅H₁₁ 1-1016 F Cl H CF₃ H NHCH₂COOCH₃ 1-1017 F Cl H CF₃ H NHCH₂COOC₂H₅ 1-1018 F Cl H CF₃ H NHCH₂COO^(n)C₃H₇ 1-1019 F Cl H CF₃ H NHCH₂COO^(n)C₄H₉ 1-1020 F Cl H CF₃ H NHCH₂COO^(n)C₅H₁₁ 1-1021 F Cl H CF₃ H NHCH₂COO^(i)C₃H₇ 1-1022 F Cl H CF₃ H NHCH₂COO^(c)C₅H₉ 1-1023 F Br H CF₃ H NH₂ 1-1024 H F H CF₃ H OH 1-1025 H Cl H CF₃ H OH 1-1026 H Br H CF₃ H OH 1-1027 F F H CF₃ H OH 1-1028 F Cl H CF₃ H OH 1-1029 F Br H CF₃ H OH 1-1030 H Cl H CF₃ H NHCH₃ 1-1031 H Cl H CF₃ H NHC₂H₅ 1-1032 H Cl H CF₃ H NHCH₂CH═CH₂ 1-1033 H Cl H CF₃ H NHCH₂C≡CH 1-1034 H Cl H CF₃ H NHCH(CH₃)C≡CH 1-1035 H Cl H CF₃ H NHSO₂CH₃ 1-1036 H Cl H CF₃ H NHSO₂C₂H₅ 1-1037 H Cl H CF₃ H NHSO₂CH₂Cl 1-1038 H Cl H CF₃ H NHSO₂CF₃ 1-1039 H Cl H CF₃ H N(CH₃)SO₂CH₃ 1-1040 H Cl H CF₃ H N(CH₂C≡CH)SO₂CH₃ 1-1041 H Cl H CF₃ H NHCOOCH₃ 1-1042 H Cl H CF₃ H NHCOOC₂H₅ 1-1043 H Cl H CF₃ H NHCOO^(n)C₃H₇ 1-1044 H Cl H CF₃ H NHCOO^(i)C₃H₇ 1-1045 H Cl H CF₃ H NHCOO^(n)C₄H₉ 1-1046 H Cl H CF₃ H NHCOO^(n)C₅H₁₁ 1-1047 H Cl H CF₃ H NHCH₂COOCH₃ 1-1048 H Cl H CF₃ H NHCH₂COOC₂H₅ 1-1049 H Cl H CF₃ H NHCH₂COO^(n)C₃H₇ 1-1050 H Cl H CF₃ H NHCH₂COO^(n)C₄H₉ 1-1051 H Cl H CF₃ H NHCH₂COO^(n)C₅H₁₁ 1-1052 H Cl H CF₃ H NHCH₂COO^(i)C₃H₇ 1-1053 H Cl H CF₃ H NHCH₂COO^(c)C₅H₉ 1-1054 H Cl H CF₃ H NHCH₂COO^(c)C₆H₁₁ 1-1055 F Cl H CF₃ H NHCH₂COO^(c)C₆H₁₁ 1-1056 F Cl H CF₃ H NHCH(CH₃)COOCH₃ 1-1057 F Cl H CF₃ H NHCH(CH₃)COOC₂H₅ 1-1058 F Cl H CF₃ H NHCH(CH₃)COO^(n)C₃H₇ 1-1059 F Cl H CF₃ H NHCH(CH₃)COO^(n)C₄H₉ 1-1060 F Cl H CF₃ H NHCH(CH₃)COO^(n)C₅H₁₁ 1-1061 F Cl H CF₃ H NHCH(CH₃)COO^(i)C₃H₇ 1-1062 F Cl H CF₃ H NHCH(CH₃)COO^(c)C₅H₉ 1-1063 F Cl H CF₃ H NHCH(CH₃)COO^(c)C₆H₁₁ 1-1064 H Cl H CF₃ H OCH₃ 1-1065 H Cl H CF₃ H OC₂H₅ 1-1066 H Cl H CF₃ H O^(i)C₃H₇ 1-1067 H Cl H CF₃ H O^(n)C₃H₇ 1-1068 H Cl H CF₃ H OCH₂CH₂Cl 1-1069 H Cl H CF₃ H OCF₂CF₂H 1-1070 H Cl H CF₃ H O^(c)C₅H₉ 1-1071 H Cl H CF₃ H O^(c)C₆H₁₁ 1-1072 H Cl H CF₃ H OCH₂CH═CH₂ 1-1073 H Cl H CF₃ H OCH₂CCl═CH₂ 1-1074 H Cl H CF₃ H OCH₂CCl═CHCl 1-1075 H Cl H CF₃ H OCH(CH₃)CH═CH₂ 1-1076 H Cl H CF₃ H OCH₂C≡CH 1-1077 H Cl H CF₃ H OCH(CH₃)C≡CH 1-1078 H Cl H CF₃ H OCH₂C≡CBr 1-1079 H Cl H CF₃ H OCH₂C≡CCl 1-1080 H Cl H CF₃ H OCH₂C≡CCH₂Cl 1-1081 H Cl H CF₃ H OCH₂CN 1-1082 H Cl H CF₃ H OCH₂OCH₃ 1-1083 H Cl H CF₃ H OCH₂OC₂H₅ 1-1084 H Cl H CF₃ H OCH₂SCH₃ 1-1085 H Cl H CF₃ H OCH₂COOCH₃ 1-1086 H Cl H CF₃ H OCH₂COOC₂H₅ 1-1087 H Cl H CF₃ H OCH₂COO^(n)C₃H₇ 1-1088 H Cl H CF₃ H OCH₂COO^(n)C₄H₉ 1-1089 H Cl H CF₃ H OCH₂COO^(n)C₅H₁₁ 1-1090 H Cl H CF₃ H OCH₂COO^(i)C₃H₇ 1-1091 H Cl H CF₃ H OCH₂COO^(c)C₅H₉ 1-1092 H Cl H CF₃ H OCH₂COO^(c)C₆H₁₁ 1-1093 H Cl H CF₃ H OCH(CH₃)COOCH₃ 1-1094 H Cl H CF₃ H OCH(CH₃)COOC₂H₅ 1-1095 H Cl H CF₃ H OCH(CH₃)COO^(n)C₃H₇ 1-1096 H Cl H CF₃ H OCH(CH₃)COO^(n)C₄H₉ 1-1097 H Cl H CF₃ H OCH(CH₃)COO^(n)C₅H₁₁ 1-1098 H Cl H CF₃ H OCH(CH₃)COO^(i)C₃H₇ 1-1099 H Cl H CF₃ H OCH(CH₃)COO^(c)C₅H₉ 1-1100 H Cl H CF₃ H OCH(CH₃)COO^(c)C₆H₁₁ 1-1101 H Cl H CF₃ H OCH₂CON(CH₃)₂ 1-1102 H Cl H CF₃ H OCH₂CON(C₂H₅)₂ 1-1103 H Cl H CF₃ H OCH₂CON(CH₃)C₂H₅ 1-1104 H Cl H CF₃ H OCH(CH₃)CON(CH₃)₂ 1-1105 H Cl H CF₃ H OCH(CH₃)CON(C₂H₅)₂ 1-1106 H Cl H CF₃ H OCH(CH₃)CON(CH₃)C₂H₅ 1-1107 H Cl H CF₃ H OCH₂COON(CH₃)₂ 1-1108 H Cl H CF₃ H OCH₂COON(C₂H₅)₂ 1-1109 H Cl H CF₃ H OCH(CH₃)COON(CH₃)₂ 1-1110 H Cl H CF₃ H OCH(CH₃)COON(C₂H₅)₂ 1-1111 F Cl H CF₃ H OCH₃ 1-1112 F Cl H CF₃ H OC₂H₅ 1-1113 F Cl H CF₃ H O^(i)C₃H₇ 1-1114 F Cl H CF₃ H O^(n)C₃H₇ 1-1115 F Cl H CF₃ H OCH₂CH₂Cl 1-1116 F Cl H CF₃ H OCF₂CF₂H 1-1117 F Cl H CF₃ H O^(c)C₅H₉ 1-1118 F Cl H CF₃ H O^(c)C₆H₁₁ 1-1119 F Cl H CF₃ H OCH₂CH═CH₂ 1-1120 F Cl H CF₃ H OCH₂CCl═CH₂ 1-1121 F Cl H CF₃ H OCH₂CCl═CHCl 1-1122 F Cl H CF₃ H OCH(CH₃)CH═CH₂ 1-1123 F Cl H CF₃ H OCH₂C≡CH 1-1124 F Cl H CF₃ H OCH(CH₃)C≡CH 1-1125 F Cl H CF₃ H OCH₂C≡CBr 1-1126 F Cl H CF₃ H OCH₂C≡CCl 1-1127 F Cl H CF₃ H OCH₂C≡CCH₂Cl 1-1128 F Cl H CF₃ H OCH₂CN 1-1129 F Cl H CF₃ H OCH₂OCH₃ 1-1130 F Cl H CF₃ H OCH₂OC₂H₅ 1-1131 F Cl H CF₃ H OCH₂SCH₃ 1-1132 F Cl H CF₃ H OCH₂COOCH₃ 1-1133 F Cl H CF₃ H OCH₂COOC₂H₅ 1-1134 F Cl H CF₃ H OCH₂COO^(n)C₃H₇ 1-1135 F Cl H CF₃ H OCH₂COO^(n)C₄H₉ 1-1136 F Cl H CF₃ H OCH₂COO^(n)C₅H₁₁ 1-1137 F Cl H CF₃ H OCH₂COO^(i)C₃H₇ 1-1138 F Cl H CF₃ H OCH₂COO^(c)C₅H₉ 1-1139 F Cl H CF₃ H OCH₂COO^(c)C₆H₁₁ 1-1140 F Cl H CF₃ H OCH(CH₃)COOCH₃ 1-1141 F Cl H CF₃ H OCH(CH₃)COOC₂H₅ 1-1142 F Cl H CF₃ H OCH(CH₃)COO^(n)C₃H₇ 1-1143 F Cl H CF₃ H OCH(CH₃)COO^(n)C₄H₉ 1-1144 F Cl H CF₃ H OCH(CH₃)COO^(n)C₅H₁₁ 1-1145 F Cl H CF₃ H OCH(CH₃)COO^(i)C₃H₇ 1-1146 F Cl H CF₃ H OCH(CH₃)COO^(c)C₅H₉ 1-1147 F Cl H CF₃ H OCH(CH₃)COO^(c)C₆H₁₁ 1-1148 F Cl H CF₃ H OCH₂CON(CH₃)₂ 1-1149 F Cl H CF₃ H OCH₂CON(C₂H₅)₂ 1-1150 F Cl H CF₃ H OCH₂CON(CH₃)C₂H₅ 1-1151 F Cl H CF₃ H OCH(CH₃)CON(CH₃)₂ 1-1152 F Cl H CF₃ H OCH(CH₃)CON(C₂H₅)₂ 1-1153 F Cl H CF₃ H OCH(CH₃)CON(CH₃)C₂H₅ 1-1154 F Cl H CF₃ H OCH₂COON(CH₃)₂ 1-1155 F Cl H CF₃ H OCH₂COON(C₂H₅)₂ 1-1156 F Cl H CF₃ H OCH(CH₃)COON(CH₃)₂ 1-1157 F Cl H CF₃ H OCH(CH₃)COON(C₂H₅)₂ 1-1158 H F H CF₃ H SH 1-1159 H Cl H CF₃ H SH 1-1160 H Br H CF₃ H SH 1-1161 F F H CF₃ H SH 1-1162 F Cl H CF₃ H SH 1-1163 F Br H CF₃ H SH 1-1164 H Cl H CF₃ H SCH₃ 1-1165 H Cl H CF₃ H SC₂H₅ 1-1166 H Cl H CF₃ H S^(i)C₃H₇ 1-1167 H Cl H CF₃ H SCH₂CH₂Cl 1-1168 H Cl H CF₃ H S^(c)C₅H₉ 1-1169 H Cl H CF₃ H S^(c)C₆H₁₁ 1-1170 H Cl H CF₃ H SCH₂CH═CH₂ 1-1171 H Cl H CF₃ H SCH₂CCl═CH₂ 1-1172 H Cl H CF₃ H SCH₂CCl═CHCl 1-1173 H Cl H CF₃ H SCH(CH₃)CH═CH₂ 1-1174 H Cl H CF₃ H SCH₂C≡CH 1-1175 H Cl H CF₃ H SCH(CH₃)C≡CH 1-1176 H Cl H CF₃ H SCH₂COOCH₃ 1-1177 H Cl H CF₃ H SCH₂COOC₂H₅ 1-1178 H Cl H CF₃ H SCH₂COO^(n)C₃H₇ 1-1179 H Cl H CF₃ H SCH₂COO^(n)C₄H₉ 1-1180 H Cl H CF₃ H SCH₂COO^(n)C₅H₁₁ 1-1181 H Cl H CF₃ H SCH₂COO^(i)C₃H₇ 1-1182 H Cl H CF₃ H SCH₂COO^(c)C₅H₉ 1-1183 H Cl H CF₃ H SCH₂COO^(c)C₆H₁₁ 1-1184 H Cl H CF₃ H SCH(CH₃)COOCH₃ 1-1185 H Cl H CF₃ H SCH(CH₃)COOC₂H₅ 1-1186 H Cl H CF₃ H SCH(CH₃)COO^(n)C₃H₇ 1-1187 H Cl H CF₃ H SCH(CH₃)COO^(n)C₄H₉ 1-1188 H Cl H CF₃ H SCH(CH₃)COO^(n)C₅H₁₁ 1-1189 H Cl H CF₃ H SCH(CH₃)COO^(i)C₃H₇ 1-1190 H Cl H CF₃ H SCH(CH₃)COO^(c)C₅H₉ 1-1191 H Cl H CF₃ H SCH(CH₃)COO^(c)C₆H₁₁ 1-1192 H Cl H CF₃ H SCH₂CON(CH₃)₂ 1-1193 H Cl H CF₃ H SCH₂CON(C₂H₅)₂ 1-1194 H Cl H CF₃ H SCH₂CON(tetramethylene) 1-1195 H Cl H CF₃ H SCH₂CON(pentamethylene) 1-1196 H Cl H CF₃ H SCH₂CON(ethyleneoxyethylene) 1-1197 H Cl H CF₃ H SCH(CH₃)CON(CH₃)₂ 1-1198 H Cl H CF₃ H SCH(CH₃)CON(C₂H₅)₂ 1-1199 H Cl H CF₃ H SCH(CH₃)CON(tetramethylene) 1-1200 H Cl H CF₃ H SCH(CH₃)CON(pentamethylene) 1-1201 F Cl H CF₃ H SCH₃ 1-1202 F Cl H CF₃ H SC₂H₅ 1-1203 F Cl H CF₃ H S^(i)C₃H₇ 1-1204 F Cl H CF₃ H SCH₂CH₂Cl 1-1205 F Cl H CF₃ H S^(c)C₅H₉ 1-1206 F Cl H CF₃ H S^(c)C₆H₁₁ 1-1207 F Cl H CF₃ H SCH₂CH═CH₂ 1-1208 F Cl H CF₃ H SCH₂CCl═CH₂ 1-1209 F Cl H CF₃ H SCH₂CCl═CHCl 1-1210 F Cl H CF₃ H SCH(CH₃)CH═CH₂ 1-1211 F Cl H CF₃ H SCH₂C≡CH 1-1212 F Cl H CF₃ H SCH(CH₃)C≡CH 1-1213 F Cl H CF₃ H SCH₂COOCH₃ 1-1214 F Cl H CF₃ H SCH₂COOC₂H₅ 1-1215 F Cl H CF₃ H SCH₂COO^(n)C₃H₇ 1-1216 F Cl H CF₃ H SCH₂COO^(n)C₄H₉ 1-1217 F Cl H CF₃ H SCH₂COO^(n)C₅H₁₁ 1-1218 F Cl H CF₃ H SCH₂COO^(i)C₃H₇ 1-1219 F Cl H CF₃ H SCH₂COO^(c)C₅H₉ 1-1220 F Cl H CF₃ H SCH₂COO^(c)C₆H₁₁ 1-1221 F Cl H CF₃ H SCH(CH₃)COOCH₃ 1-1222 F Cl H CF₃ H SCH(CH₃)COOC₂H₅ 1-1223 F Cl H CF₃ H SCH(CH₃)COO^(n)C₃H₇ 1-1224 F Cl H CF₃ H SCH(CH₃)COO^(n)C₄H₉ 1-1225 F Cl H CF₃ H SCH(CH₃)COO^(n)C₅H₁₁ 1-1226 F Cl H CF₃ H SCH(CH₃)COO^(i)C₃H₇ 1-1227 F Cl H CF₃ H SCH(CH₃)COO^(c)C₅H₉ 1-1228 F Cl H CF₃ H SCH(CH₃)COO^(c)C₆H₁₁ 1-1229 F Cl H CF₃ H SCH₂CON(CH₃)₂ 1-1230 F Cl H CF₃ H SCH₂CON(C₂H₅)₂ 1-1231 F Cl H CF₃ H SCH₂CON(tetramethylene) 1-1232 F Cl H CF₃ H SCH₂CON(pentamethylene) 1-1233 F Cl H CF₃ H SCH₂CON(ethyleneoxyethylene) 1-1234 F Cl H CF₃ H SCH(CH₃)CON(CH₃)₂ 1-1235 F Cl H CF₃ H SCH(CH₃)CON(C₂H₅)₂ 1-1236 F Cl H CF₃ H SCH(CH₃)CON(tetramethylene) 1-1237 F Cl H CF₃ H SCH(CH₃)CON(pentamethylene) 1-1238 H F H CF₃ H SO₂Cl 1-1239 H Cl H CF₃ H SO₂Cl 1-1240 H Br H CF₃ H SO₂Cl 1-1241 F F H CF₃ H SO₂Cl 1-1242 F Cl H CF₃ H SO₂Cl 1-1243 F Br H CF₃ H SO₂Cl 1-1244 H Cl H CF₃ H SO₂OCH₃ 1-1245 H Cl H CF₃ H SO₂OC₂H₅ 1-1246 H Cl H CF₃ H SO₂O^(i)C₃H₇ 1-1247 H Cl H CF₃ H SO₂OCH₂CH═CH₂ 1-1248 F Cl H CF₃ H SO₂OCH₃ 1-1249 F Cl H CF₃ H SO₂OC₂H₅ 1-1250 F Cl H CF₃ H SO₂O^(i)C₃H₇ 1-1251 F Cl H CF₃ H SO₂OCH₂CH═CH₂ 1-1252 H Cl H CF₃ H SO₂N(CH₃)₂ 1-1253 H Cl H CF₃ H SO₂N(C₂H₅)₂ 1-1254 F Cl H CF₃ H SO₂N(CH₃)₂ 1-1255 F Cl H CF₃ H SO₂N(C₂H₅)₂ 1-1256 H Cl H CF₃ H COOH 1-1257 H Cl H CF₃ H COOCH₃ 1-1258 H Cl H CF₃ H COOC₂H₅ 1-1259 H Cl H CF₃ H COO^(n)C₃H₇ 1-1260 H Cl H CF₃ H COO^(n)C₄H₉ 1-1261 H Cl H CF₃ H COO^(n)C₅H₁₁ 1-1262 H Cl H CF₃ H COO^(i)C₃H₇ 1-1263 H Cl H CF₃ H COOCH₂CH₂Cl 1-1264 H Cl H CF₃ H COOCH₂CH₂Br 1-1265 H Cl H CF₃ H CON(CH₃)₂ 1-1266 H Cl H CF₃ H CONHCH₃ 1-1267 H Cl H CF₃ H CON(C₂H₅)₂ 1-1268 H Cl H CF₃ H CONHC₂H₅ 1-1269 H Cl H CF₃ H COCH₃ 1-1270 H Cl H CF₃ H COC₂H₅ 1-1271 H Cl H CF₃ H COCH₂Cl 1-1272 H Cl H CF₃ H CHO 1-1273 H Cl H CF₃ H CH═CHCOOCH₃ 1-1274 H Cl H CF₃ H CH═CHCOOC₂H₅ 1-1275 H Cl H CF₃ H CH₂CH₂COOCH₃ 1-1276 H Cl H CF₃ H CH₂CH₂COOC₂H₅ 1-1277 F Cl H CF₃ H COOH 1-1278 F Cl H CF₃ H COOCH₃ 1-1279 F Cl H CF₃ H COOC₂H₅ 1-1280 F Cl H CF₃ H COO^(n)C₃H₇ 1-1281 F Cl H CF₃ H COO^(n)C₄H₉ 1-1282 F Cl H CF₃ H COO^(n)C₅H₁₁ 1-1283 F Cl H CF₃ H COO^(i)C₃H₇ 1-1284 F Cl H CF₃ H COOCH₂CH₂Cl 1-1285 F Cl H CF₃ H COOCH₂CH₂Br 1-1286 F Cl H CF₃ H CON(CH₃)₂ 1-1287 F Cl H CF₃ H CONHCH₃ 1-1288 F Cl H CF₃ H CON(C₂H₅)₂ 1-1289 F Cl H CF₃ H CONHC₂H₅ 1-1290 F Cl H CF₃ H COCH₃ 1-1291 F Cl H CF₃ H COC₂H₅ 1-1292 F Cl H CF₃ H COCH₂Cl 1-1293 F Cl H CF₃ H CHO 1-1294 F Cl H CF₃ H CH═CHCOOCH₃ 1-1295 F Cl H CF₃ H CH═CHCOOC₂H₅ 1-1296 F Cl H CF₃ H CH₂CH₂COOCH₃ 1-1297 F Cl H CF₃ H CH₂CH₂COOC₂H₅ 1-1298 H F CH₃ CF₃ H NO₂ 1-1299 H Cl CH₃ CF₃ H NO₂ 1-1300 H Br CH₃ CF₃ H NO₂ 1-1301 F F CH₃ CF₃ H NO₂ 1-1302 F Cl CH₃ CF₃ H NO₂ 1-1303 F Br CH₃ CF₃ H NO₂ 1-1304 H F CH₃ CF₃ H NH₂ 1-1305 H Cl CH₃ CF₃ H NH₂ 1-1306 H Br CH₃ CF₃ H NH₂ 1-1307 F F CH₃ CF₃ H NH₂ 1-1308 F Cl CH₃ CF₃ H NH₂ 1-1309 H Cl CH₃ CF₃ H NHCH(CH₃)COOCH₃ 1-1310 H Cl CH₃ CF₃ H NHCH(CH₃)COOC₂H₅ 1-1311 H Cl CH₃ CF₃ H NHCH(CH₃)COO^(n)C₃H₇ 1-1312 H Cl CH₃ CF₃ H NHCH(CH₃)COO^(n)C₄H₉ 1-1313 H Cl CH₃ CF₃ H NHCH(CH₃)COO^(n)C₅H₁₁ 1-1314 H Cl CH₃ CF₃ H NHCH(CH₃)COO^(i)C₃H₇ 1-1315 H Cl CH₃ CF₃ H NHCH(CH₃)COO^(c)C₅H₉ 1-1316 H Cl CH₃ CF₃ H NHCH(CH₃)COO^(c)C₆H₁₁ 1-1317 F Cl CH₃ CF₃ H NHCH₃ 1-1318 F Cl CH₃ CF₃ H NHC₂H₅ 1-1319 F Cl CH₃ CF₃ H NHCH₂CH═CH₂ 1-1320 F Cl CH₃ CF₃ H NHCH₂C≡CH 1-1321 F Cl CH₃ CF₃ H NHCH(CH₃)C≡CH 1-1322 F Cl CH₃ CF₃ H NHSO₂CH₃ 1-1323 F Cl CH₃ CF₃ H NHSO₂C₂H₅ 1-1324 F Cl CH₃ CF₃ H NHSO₂CH₂Cl 1-1325 F Cl CH₃ CF₃ H NHSO₂CF₃ 1-1326 F Cl CH₃ CF₃ H N(CH₃)SO₂CH₃ 1-1327 F Cl CH₃ CF₃ H N(CH₂C≡CH)SO₂CH₃ 1-1328 F Cl CH₃ CF₃ H NHCOOCH₃ 1-1329 F Cl CH₃ CF₃ H NHCOOC₂H₅ 1-1330 F Cl CH₃ CF₃ H NHCOO^(n)C₃H₇ 1-1331 F Cl CH₃ CF₃ H NHCOO^(i)C₃H₇ 1-1332 F Cl CH₃ CF₃ H NHCOO^(n)C₄H₉ 1-1333 F Cl CH₃ CF₃ H NHCOO^(n)C₅H₁₁ 1-1334 F Cl CH₃ CF₃ H NHCH₂COOCH₃ 1-1335 F Cl CH₃ CF₃ H NHCH₂COOC₂H₅ 1-1336 F Cl CH₃ CF₃ H NHCH₂COO^(n)C₃H₇ 1-1337 F Cl CH₃ CF₃ H NHCH₂COO^(n)C₄H₉ 1-1338 F Cl CH₃ CF₃ H NHCH₂COO^(n)C₅H₁₁ 1-1339 F Cl CH₃ CF₃ H NHCH₂COO^(i)C₃H₇ 1-1340 F Cl CH₃ CF₃ H NHCH₂COO^(c)C₅H₉ 1-1341 F Br CH₃ CF₃ H NH₂ 1-1342 H F CH₃ CF₃ H OH 1-1343 H Cl CH₃ CF₃ H OH 1-1344 H Br CH₃ CF₃ H OH 1-1345 F F CH₃ CF₃ H OH 1-1346 F Cl CH₃ CF₃ H OH 1-1347 F Br CH₃ CF₃ H OH 1-1348 H Cl CH₃ CF₃ H NHCH₃ 1-1349 H Cl CH₃ CF₃ H NHC₂H₅ 1-1350 H Cl CH₃ CF₃ H NHCH₂CH═CH₂ 1-1351 H Cl CH₃ CF₃ H NHCH₂C≡CH 1-1352 H Cl CH₃ CF₃ H NHCH(CH₃)C≡CH 1-1353 H Cl CH₃ CF₃ H NHSO₂CH₃ 1-1354 H Cl CH₃ CF₃ H NHSO₂C₂H₅ 1-1355 H Cl CH₃ CF₃ H NHSO₂CH₂Cl 1-1356 H Cl CH₃ CF₃ H NHSO₂CF₃ 1-1357 H Cl CH₃ CF₃ H N(CH₃)SO₂CH₃ 1-1358 H Cl CH₃ CF₃ H N(CH₂C≡CH)SO₂CH₃ 1-1359 H Cl CH₃ CF₃ H NHCOOCH₃ 1-1360 H Cl CH₃ CF₃ H NHCOOC₂H₅ 1-1361 H Cl CH₃ CF₃ H NHCOO^(n)C₃H₇ 1-1362 H Cl CH₃ CF₃ H NHCOO^(i)C₃H₇ 1-1363 H Cl CH₃ CF₃ H NHCOO^(n)C₄H₉ 1-1364 H Cl CH₃ CF₃ H NHCOO^(n)C₅H₁₁ 1-1365 H Cl CH₃ CF₃ H NHCH₂COOCH₃ 1-1366 H Cl CH₃ CF₃ H NHCH₂COOC₂H₅ 1-1367 H Cl CH₃ CF₃ H NHCH₂COO^(n)C₃H₇ 1-1368 H Cl CH₃ CF₃ H NHCH₂COO^(n)C₄H₉ 1-1369 H Cl CH₃ CF₃ H NHCH₂COO^(n)C₅H₁₁ 1-1370 H Cl CH₃ CF₃ H NHCH₂COO^(i)C₃H₇ 1-1371 H Cl CH₃ CF₃ H NHCH₂COO^(c)C₅H₉ 1-1372 H Cl CH₃ CF₃ H NHCH₂COO^(c)C₆H₁₁ 1-1373 F Cl CH₃ CF₃ H NHCH₂COO^(c)C₆H₁₁ 1-1374 F Cl CH₃ CF₃ H NHCH(CH₃)COOCH₃ 1-1375 F Cl CH₃ CF₃ H NHCH(CH₃)COOC₂H₅ 1-1376 F Cl CH₃ CF₃ H NHCH(CH₃)COO^(n)C₃H₇ 1-1377 F Cl CH₃ CF₃ H NHCH(CH₃)COO^(n)C₄H₉ 1-1378 F Cl CH₃ CF₃ H NHCH(CH₃)COO^(n)C₅H₁₁ 1-1379 F Cl CH₃ CF₃ H NHCH(CH₃)COO^(i)C₃H₇ 1-1380 F Cl CH₃ CF₃ H NHCH(CH₃)COO^(c)C₅H₉ 1-1381 F Cl CH₃ CF₃ H NHCH(CH₃)COO^(c)C₆H₁₁ 1-1382 H Cl CH₃ CF₃ H OCH₃ 1-1383 H Cl CH₃ CF₃ H OC₂H₅ 1-1384 H Cl CH₃ CF₃ H O^(i)C₃H₇ 1-1385 H Cl CH₃ CF₃ H O^(n)C₃H₇ 1-1386 H Cl CH₃ CF₃ H OCH₂CH₂Cl 1-1387 H Cl CH₃ CF₃ H OCF₂CF₂H 1-1388 H Cl CH₃ CF₃ H O^(c)C₅H₉ 1-1389 H Cl CH₃ CF₃ H O^(c)C₆H₁₁ 1-1390 H Cl CH₃ CF₃ H OCH₂CH═CH₂ 1-1391 H Cl CH₃ CF₃ H OCH₂CCl═CH₂ 1-1392 H Cl CH₃ CF₃ H OCH₂CCl═CHCl 1-1393 H Cl CH₃ CF₃ H OCH(CH₃)CH═CH₂ 1-1394 H Cl CH₃ CF₃ H OCH₂C≡CH 1-1395 H Cl CH₃ CF₃ H OCH(CH₃)C≡CH 1-1396 H Cl CH₃ CF₃ H OCH₂C≡CBr 1-1397 H Cl CH₃ CF₃ H OCH₂C≡CCl 1-1398 H Cl CH₃ CF₃ H OCH₂C≡CCH₂Cl 1-1399 H Cl CH₃ CF₃ H OCH₂CN 1-1400 H Cl CH₃ CF₃ H OCH₂OCH₃ 1-1401 H Cl CH₃ CF₃ H OCH₂OC₂H₅ 1-1402 H Cl CH₃ CF₃ H OCH₂SCH₃ 1-1403 H Cl CH₃ CF₃ H OCH₂COOCH₃ 1-1404 H Cl CH₃ CF₃ H OCH₂COOC₂H₅ 1-1405 H Cl CH₃ CF₃ H OCH₂COO^(n)C₃H₇ 1-1406 H Cl CH₃ CF₃ H OCH₂COO^(n)C₄H₉ 1-1407 H Cl CH₃ CF₃ H OCH₂COO^(n)C₅H₁₁ 1-1408 H Cl CH₃ CF₃ H OCH₂COO^(i)C₃H₇ 1-1409 H Cl CH₃ CF₃ H OCH₂COO^(c)C₅H₉ 1-1410 H Cl CH₃ CF₃ H OCH₂COO^(c)C₆H₁₁ 1-1411 H Cl CH₃ CF₃ H OCH(CH₃)COOCH₃ 1-1412 H Cl CH₃ CF₃ H OCH(CH₃)COOC₂H₅ 1-1413 H Cl CH₃ CF₃ H OCH(CH₃)COO^(n)C₃H₇ 1-1414 H Cl CH₃ CF₃ H OCH(CH₃)COO^(n)C₄H₉ 1-1415 H Cl CH₃ CF₃ H OCH(CH₃)COO^(n)C₅H₁₁ 1-1416 H Cl CH₃ CF₃ H OCH(CH₃)COO^(i)C₃H₇ 1-1417 H Cl CH₃ CF₃ H OCH(CH₃)COO^(c)C₅H₉ 1-1418 H Cl CH₃ CF₃ H OCH(CH₃)COO^(c)C₆H₁₁ 1-1419 H Cl CH₃ CF₃ H OCH₂CON(CH₃)₂ 1-1420 H Cl CH₃ CF₃ H OCH₂CON(C₂H₅)₂ 1-1421 H Cl CH₃ CF₃ H OCH₂CON(CH₃)C₂H₅ 1-1422 H Cl CH₃ CF₃ H OCH(CH₃)CON(CH₃)₂ 1-1423 H Cl CH₃ CF₃ H OCH(CH₃)CON(C₂H₅)₂ 1-1424 H Cl CH₃ CF₃ H OCH(CH₃)CON(CH₃)C₂H₅ 1-1425 H Cl CH₃ CF₃ H OCH₂COON(CH₃)₂ 1-1426 H Cl CH₃ CF₃ H OCH₂COON(C₂H₅)₂ 1-1427 H Cl CH₃ CF₃ H OCH(CH₃)COON(CH₃)₂ 1-1428 H Cl CH₃ CF₃ H OCH(CH₃)COON(C₂H₅)₂ 1-1429 F Cl CH₃ CF₃ H OCH₃ 1-1430 F Cl CH₃ CF₃ H OC₂H₅ 1-1431 F Cl CH₃ CF₃ H O^(i)C₃H₇ 1-1432 F Cl CH₃ CF₃ H O^(n)C₃H₇ 1-1433 F Cl CH₃ CF₃ H OCH₂CH₂Cl 1-1434 F Cl CH₃ CF₃ H OCF₂CF₂H 1-1435 F Cl CH₃ CF₃ H O^(c)C₅H₉ 1-1436 F Cl CH₃ CF₃ H O^(c)C₆H₁₁ 1-1437 F Cl CH₃ CF₃ H OCH₂CH═CH₂ 1-1438 F Cl CH₃ CF₃ H OCH₂CCl═CH₂ 1-1439 F Cl CH₃ CF₃ H OCH₂CCl═CHCl 1-1440 F Cl CH₃ CF₃ H OCH(CH₃)CH═CH₂ 1-1441 F Cl CH₃ CF₃ H OCH₂C≡CH 1-1442 F Cl CH₃ CF₃ H OCH(CH₃)C≡CH 1-1443 F Cl CH₃ CF₃ H OCH₂C≡CBr 1-1444 F Cl CH₃ CF₃ H OCH₂C≡CCl 1-1445 F Cl CH₃ CF₃ H OCH₂C≡CCH₂Cl 1-1446 F Cl CH₃ CF₃ H OCH₂CN 1-1447 F Cl CH₃ CF₃ H OCH₂OCH₃ 1-1448 F Cl CH₃ CF₃ H OCH₂OC₂H₅ 1-1449 F Cl CH₃ CF₃ H OCH₂SCH₃ 1-1450 F Cl CH₃ CF₃ H OCH₂COOCH₃ 1-1451 F Cl CH₃ CF₃ H OCH₂COOC₂H₅ 1-1452 F Cl CH₃ CF₃ H OCH₂COO^(n)C₃H₇ 1-1453 F Cl CH₃ CF₃ H OCH₂COO^(n)C₄H₉ 1-1454 F Cl CH₃ CF₃ H OCH₂COO^(n)C₅H₁₁ 1-1455 F Cl CH₃ CF₃ H OCH₂COO^(i)C₃H₇ 1-1456 F Cl CH₃ CF₃ H OCH₂COO^(c)C₅H₉ 1-1457 F Cl CH₃ CF₃ H OCH₂COO^(c)C₆H₁₁ 1-1458 F Cl CH₃ CF₃ H OCH(CH₃)COOCH₃ 1-1459 F Cl CH₃ CF₃ H OCH(CH₃)COOC₂H₅ 1-1460 F Cl CH₃ CF₃ H OCH(CH₃)COO^(n)C₃H₇ 1-1461 F Cl CH₃ CF₃ H OCH(CH₃)COO^(n)C₄H₉ 1-1462 F Cl CH₃ CF₃ H OCH(CH₃)COO^(n)C₅H₁₁ 1-1463 F Cl CH₃ CF₃ H OCH(CH₃)COO^(i)C₃H₇ 1-1464 F Cl CH₃ CF₃ H OCH(CH₃)COO^(c)C₅H₉ 1-1465 F Cl CH₃ CF₃ H OCH(CH₃)COO^(c)C₆H₁₁ 1-1466 F Cl CH₃ CF₃ H OCH₂CON(CH₃)₂ 1-1467 F Cl CH₃ CF₃ H OCH₂CON(C₂H₅)₂ 1-1468 F Cl CH₃ CF₃ H OCH₂CON(CH₃)C₂H₅ 1-1469 F Cl CH₃ CF₃ H OCH(CH₃)CON(CH₃)₂ 1-1470 F Cl CH₃ CF₃ H OCH(CH₃)CON(C₂H₅)₂ 1-1471 F Cl CH₃ CF₃ H OCH(CH₃)CON(CH₃)C₂H₅ 1-1472 F Cl CH₃ CF₃ H OCH₂COON(CH₃)₂ 1-1473 F Cl CH₃ CF₃ H OCH₂COON(C₂H₅)₂ 1-1474 F Cl CH₃ CF₃ H OCH(CH₃)COON(CH₃)₂ 1-1475 F Cl CH₃ CF₃ H OCH(CH₃)COON(C₂H₅)₂ 1-1476 H F CH₃ CF₃ H SH 1-1477 H Cl CH₃ CF₃ H SH 1-1478 H Br CH₃ CF₃ H SH 1-1479 F F CH₃ CF₃ H SH 1-1480 F Cl CH₃ CF₃ H SH 1-1481 F Br CH₃ CF₃ H SH 1-1482 H Cl CH₃ CF₃ H SCH₃ 1-1483 H Cl CH₃ CF₃ H SC₂H₅ 1-1484 H Cl CH₃ CF₃ H S^(i)C₃H₇ 1-1485 H Cl CH₃ CF₃ H SCH₂CH₂Cl 1-1486 H Cl CH₃ CF₃ H S^(c)C₅H₉ 1-1487 H Cl CH₃ CF₃ H S^(c)C₆H₁₁ 1-1488 H Cl CH₃ CF₃ H SCH₂CH═CH₂ 1-1489 H Cl CH₃ CF₃ H SCH₂CCl═CH₂ 1-1490 H Cl CH₃ CF₃ H SCH₂CCl═CHCl 1-1491 H Cl CH₃ CF₃ H SCH(CH₃)CH═CH₂ 1-1492 H Cl CH₃ CF₃ H SCH₂C≡CH 1-1493 H Cl CH₃ CF₃ H SCH(CH₃)C≡CH 1-1494 H Cl CH₃ CF₃ H SCH₂COOCH₃ 1-1495 H Cl CH₃ CF₃ H SCH₂COOC₂H₅ 1-1496 H Cl CH₃ CF₃ H SCH₂COO^(n)C₃H₇ 1-1497 H Cl CH₃ CF₃ H SCH₂COO^(n)C₄H₉ 1-1498 H Cl CH₃ CF₃ H SCH₂COO^(n)C₅H₁₁ 1-1499 H Cl CH₃ CF₃ H SCH₂COO^(i)C₃H₇ 1-1500 H Cl CH₃ CF₃ H SCH₂COO^(c)C₅H₉ 1-1501 H Cl CH₃ CF₃ H SCH₂COO^(c)C₆H₁₁ 1-1502 H Cl CH₃ CF₃ H SCH(CH₃)COOCH₃ 1-1503 H Cl CH₃ CF₃ H SCH(CH₃)COOC₂H₅ 1-1504 H Cl CH₃ CF₃ H SCH(CH₃)COO^(n)C₃H₇ 1-1505 H Cl CH₃ CF₃ H SCH(CH₃)COO^(n)C₄H₉ 1-1506 H Cl CH₃ CF₃ H SCH(CH₃)COO^(n)C₅H₁₁ 1-1507 H Cl CH₃ CF₃ H SCH(CH₃)COO^(i)C₃H₇ 1-1508 H Cl CH₃ CF₃ H SCH(CH₃)COO^(c)C₅H₉ 1-1509 H Cl CH₃ CF₃ H SCH(CH₃)COO^(c)C₆H₁₁ 1-1510 H Cl CH₃ CF₃ H SCH₂CON(CH₃)₂ 1-1511 H Cl CH₃ CF₃ H SCH₂CON(C₂H₅)₂ 1-1512 H Cl CH₃ CF₃ H SCH₂CON(tetramethylene) 1-1513 H Cl CH₃ CF₃ H SCH₂CON(pentamethylene) 1-1514 H Cl CH₃ CF₃ H SCH₂CON(ethyleneoxyethylene) 1-1515 H Cl CH₃ CF₃ H SCH(CH₃)CON(CH₃)₂ 1-1516 H Cl CH₃ CF₃ H SCH(CH₃)CON(C₂H₅)₂ 1-1517 H Cl CH₃ CF₃ H SCH(CH₃)CON(tetramethylene) 1-1518 H Cl CH₃ CF₃ H SCH(CH₃)CON(pentamethylene) 1-1519 F Cl CH₃ CF₃ H SCH₃ 1-1520 F Cl CH₃ CF₃ H SC₂H₅ 1-1521 F Cl CH₃ CF₃ H S^(i)C₃H₇ 1-1522 F Cl CH₃ CF₃ H SCH₂CH₂Cl 1-1523 F Cl CH₃ CF₃ H S^(c)C₅H₉ 1-1524 F Cl CH₃ CF₃ H S^(c)C₆H₁₁ 1-1525 F Cl CH₃ CF₃ H SCH₂CH═CH₂ 1-1526 F Cl CH₃ CF₃ H SCH₂CCl═CH₂ 1-1527 F Cl CH₃ CF₃ H SCH₂CCl═CHCl 1-1528 F Cl CH₃ CF₃ H SCH(CH₃)CH═CH₂ 1-1529 F Cl CH₃ CF₃ H SCH₂C≡CH 1-1530 F Cl CH₃ CF₃ H SCH(CH₃)C≡CH 1-1531 F Cl CH₃ CF₃ H SCH₂COOCH₃ 1-1532 F Cl CH₃ CF₃ H SCH₂COOC₂H₅ 1-1533 F Cl CH₃ CF₃ H SCH₂COO^(n)C₃H₇ 1-1534 F Cl CH₃ CF₃ H SCH₂COO^(n)C₄H₉ 1-1535 F Cl CH₃ CF₃ H SCH₂COO^(n)C₅H₁₁ 1-1536 F Cl CH₃ CF₃ H SCH₂COO^(i)C₃H₇ 1-1537 F Cl CH₃ CF₃ H SCH₂COO^(c)C₅H₉ 1-1538 F Cl CH₃ CF₃ H SCH₂COO^(c)C₆H₁₁ 1-1539 F Cl CH₃ CF₃ H SCH(CH₃)COOCH₃ 1-1540 F Cl CH₃ CF₃ H SCH(CH₃)COOC₂H₅ 1-1541 F Cl CH₃ CF₃ H SCH(CH₃)COO^(n)C₃H₇ 1-1542 F Cl CH₃ CF₃ H SCH(CH₃)COO^(n)C₄H₉ 1-1543 F Cl CH₃ CF₃ H SCH(CH₃)COO^(n)C₅H₁₁ 1-1544 F Cl CH₃ CF₃ H SCH(CH₃)COO^(i)C₃H₇ 1-1545 F Cl CH₃ CF₃ H SCH(CH₃)COO^(c)C₅H₉ 1-1546 F Cl CH₃ CF₃ H SCH(CH₃)COO^(c)C₆H₁₁ 1-1547 F Cl CH₃ CF₃ H SCH₂CON(CH₃)₂ 1-1548 F Cl CH₃ CF₃ H SCH₂CON(C₂H₅)₂ 1-1549 F Cl CH₃ CF₃ H SCH₂CON(tetramethylene) 1-1550 F Cl CH₃ CF₃ H SCH₂CON(pentamethylene) 1-1551 F Cl CH₃ CF₃ H SCH₂CON(ethyleneoxyethylene) 1-1552 F Cl CH₃ CF₃ H SCH(CH₃)CON(CH₃)₂ 1-1553 F Cl CH₃ CF₃ H SCH(CH₃)CON(C₂H₅)₂ 1-1554 F Cl CH₃ CF₃ H SCH(CH₃)CON(tetramethylene) 1-1555 F Cl CH₃ CF₃ H SCH(CH₃)CON(pentamethylene) 1-1556 H F CH₃ CF₃ H SO₂Cl 1-1557 H Cl CH₃ CF₃ H SO₂Cl 1-1558 H Br CH₃ CF₃ H SO₂Cl 1-1559 F F CH₃ CF₃ H SO₂Cl 1-1560 F Cl CH₃ CF₃ H SO₂Cl 1-1561 F Br CH₃ CF₃ H SO₂Cl 1-1562 H Cl CH₃ CF₃ H SO₂OCH₃ 1-1563 H Cl CH₃ CF₃ H SO₂OC₂H₅ 1-1564 H Cl CH₃ CF₃ H SO₂O^(i)C₃H₇ 1-1565 H Cl CH₃ CF₃ H SO₂OCH₂CH═CH₂ 1-1566 F Cl CH₃ CF₃ H SO₂OCH₃ 1-1567 F Cl CH₃ CF₃ H SO₂OC₂H₅ 1-1568 F Cl CH₃ CF₃ H SO₂O^(i)C₃H₇ 1-1569 F Cl CH₃ CF₃ H SO₂OCH₂CH═CH₂ 1-1570 H Cl CH₃ CF₃ H SO₂N(CH₃)₂ 1-1571 H Cl CH₃ CF₃ H SO₂N(C₂H₅)₂ 1-1572 F Cl CH₃ CF₃ H SO₂N(CH₃)₂ 1-1573 F Cl CH₃ CF₃ H SO₂N(C₂H₅)₂ 1-1574 H Cl CH₃ CF₃ H COOH 1-1575 H Cl CH₃ CF₃ H COOCH₃ 1-1576 H Cl CH₃ CF₃ H COOC₂H₅ 1-1577 H Cl CH₃ CF₃ H COO^(n)C₃H₇ 1-1578 H Cl CH₃ CF₃ H COO^(n)C₄H₉ 1-1579 H Cl CH₃ CF₃ H COO^(n)C₅H₁₁ 1-1580 H Cl CH₃ CF₃ H COO^(i)C₃H₇ 1-1581 H Cl CH₃ CF₃ H COOCH₂CH₂Cl 1-1582 H Cl CH₃ CF₃ H COOCH₂CH₂Br 1-1583 H Cl CH₃ CF₃ H CON(CH₃)₂ 1-1584 H Cl CH₃ CF₃ H CONHCH₃ 1-1585 H Cl CH₃ CF₃ H CON(C₂H₅)₂ 1-1586 H Cl CH₃ CF₃ H CONHC₂H₅ 1-1587 H Cl CH₃ CF₃ H COCH₃ 1-1588 H Cl CH₃ CF₃ H COC₂H₅ 1-1589 H Cl CH₃ CF₃ H COCH₂Cl 1-1590 H Cl CH₃ CF₃ H CHO 1-1591 H Cl CH₃ CF₃ H CH═CHCOOCH₃ 1-1592 H Cl CH₃ CF₃ H CH═CHCOOC₂H₅ 1-1593 H Cl CH₃ CF₃ H CH₂CH₂COOCH₃ 1-1594 H Cl CH₃ CF₃ H CH₂CH₂COOC₂H₅ 1-1595 F Cl CH₃ CF₃ H COOH 1-1596 F Cl CH₃ CF₃ H COOCH₃ 1-1597 F Cl CH₃ CF₃ H COOC₂H₅ 1-1598 F Cl CH₃ CF₃ H COO^(n)C₃H₇ 1-1599 F Cl CH₃ CF₃ H COO^(n)C₄H₉ 1-1600 F Cl CH₃ CF₃ H COO^(n)C₅H₁₁ 1-1601 F Cl CH₃ CF₃ H COO^(i)C₃H₇ 1-1602 F Cl CH₃ CF₃ H COOCH₂CH₂Cl 1-1603 F Cl CH₃ CF₃ H COOCH₂CH₂Br 1-1604 F Cl CH₃ CF₃ H CON(CH₃)₂ 1-1605 F Cl CH₃ CF₃ H CONHCH₃ 1-1606 F Cl CH₃ CF₃ H CON(C₂H₅)₂ 1-1607 F Cl CH₃ CF₃ H CONHC₂H₅ 1-1608 F Cl CH₃ CF₃ H COCH₃ 1-1609 F Cl CH₃ CF₃ H COC₂H₅ 1-1610 F Cl CH₃ CF₃ H COCH₂Cl 1-1611 F Cl CH₃ CF₃ H CHO 1-1612 F Cl CH₃ CF₃ H CH═CHCOOCH₃ 1-1613 F Cl CH₃ CF₃ H CH═CHCOOC₂H₅ 1-1614 F Cl CH₃ CF₃ H CH₂CH₂COOCH₃ 1-1615 F Cl CH₃ CF₃ H CH₂CH₂COOC₂H₅ 1-1616 H F CH₃ CF₃ H H 1-1617 H Cl CH₃ CF₃ H H 1-1618 H Br CH₃ CF₃ H H 1-1619 F F CH₃ CF₃ H H 1-1620 F Cl CH₃ CF₃ H H 1-1621 F Br CH₃ CF₃ H H 1-1622 F Cl H CF₃ CH₃ CH₂CHClCO₂C₂H₅ 1-1623 F Cl H CF₃ H CH₂CHClCO₂C₂H₅ 1-1624 F Cl H CF₃ CH₃ CH₂CHClCO₂CH₃ 1-1625 F Cl H CF₃ H CH₂CHClCO₂CH₃ 1-1626 F Cl H CF₃ H OCH₂CO₂H 1-1627 F Cl H CF₃ CH₃ OCH₂CO₂H 1-1628 F Cl CH₃ CF₃ H OCH₂CO₂H 1-1629 F Cl H CF₃ H OCH(CH₃)CO₂H 1-1630 F Cl H CF₃ CH₃ OCH(CH₃)CO₂H 1-1631 F Cl CH₃ CF₃ H OCH(CH₃)CO₂H 1-1632 H Cl H CF₃ H OCH₂CO₂H 1-1633 H Cl H CF₃ CH₃ OCH₂CO₂H 1-1634 H Cl CH₃ CF₃ H OCH₂CO₂H 1-1635 H Cl H CF₃ H OCH(CH₃)CO₂H 1-1636 H Cl H CF₃ CH₃ OCH(CH₃)CO₂H 1-1637 H Cl CH₃ CF₃ H OCH(CH₃)CO₂H 1-1638 F Cl H CF₃ H SCH₂CO₂H 1-1639 F Cl H CF₃ CH₃ SCH₂CO₂H 1-1640 F Cl CH₃ CF₃ H SCH₂CO₂H 1-1641 F Cl H CF₃ H SCH(CH₃)CO₂H 1-1642 F Cl H CF₃ CH₃ SCH(CH₃)CO₂H 1-1643 F Cl CH₃ CF₃ H SCH(CH₃)CO₂H 1-1644 H Cl H CF₃ H SCH₂CO₂H 1-1645 H Cl H CF₃ CH₃ SCH₂CO₂H 1-1646 H Cl CH₃ CF₃ H SCH₂CO₂H 1-1647 H Cl H CF₃ H SCH(CH₃)CO₂H 1-1648 H Cl H CF₃ CH₃ SCH(CH₃)CO₂H 1-1649 H Cl CH₃ CF₃ H SCH(CH₃)CO₂H 1-1650 F Cl H CF₃ CH₃ OCH(C₂H₅)CO₂CH₃ 1-1651 Cl Cl H CF₃ H OCH₂CO₂CH₃ 1-1652 Cl Cl H CF₃ H OCH₂CO₂C₂H₅ 1-1653 Cl Cl H CF₃ H OCH₂CO₂ ^(i)C₃H₇ 1-1654 Cl Cl H CF₃ CH₃ OCH₂CO₂CH₃ 1-1655 Cl Cl H CF₃ CH₃ OCH₂CO₂C₂H₅ 1-1656 Cl Cl H CF₃ CH₃ OCH₂CO₂ ^(i)C₃H₇ 1-1657 Cl Cl CH₃ CF₃ H OCH₂CO₂CH₃ 1-1658 Cl Cl CH₃ CF₃ H OCH₂CO₂C₂H₅ 1-1659 Cl Cl CH₃ CF₃ H OCH₂CO₂ ^(i)C₃H₇ 1-1660 Cl Cl H CF₃ H OCH₂C≡CH 1-1661 Cl Cl H CF₃ H OCH(CH₃)C≡CH 1-1662 Cl Cl H CF₃ H OCH(CH₃)CO₂C₂H₅ 1-1663 Cl Cl H CF₃ CH₃ OCH₂C≡CH 1-1664 Cl Cl H CF₃ CH₃ OCH(CH₃)C≡CH 1-1665 Cl Cl H CF₃ CH₃ OCH(CH₃)CO₂C₂H₅ 1-1666 Cl Cl CH₃ CF₃ H OCH₂C≡CH 1-1667 Cl Cl CH₃ CF₃ H OCH(CH₃)C≡CH 1-1668 Cl Cl CH₃ CF₃ H OCH(CH₃)CO₂C₂H₅ 1-1669 F Br H CF₃ H OCH₂CO₂CH₃ 1-1670 F Br H CF₃ H OCH₂CO₂C₂H₅ 1-1671 F Br H CF₃ H OCH₂CO₂ ^(i)C₃H₇ 1-1672 F Br H CF₃ CH₃ OCH₂CO₂CH₃ 1-1673 F Br H CF₃ CH₃ OCH₂CO₂C₂H₅ 1-1674 F Br H CF₃ CH₃ OCH₂CO₂ ^(i)C₃H₇ 1-1675 F Br CH₃ CF₃ H OCH₂CO₂CH₃ 1-1676 F Br CH₃ CF₃ H OCH₂CO₂C₂H₅ 1-1677 F Br CH₃ CF₃ H OCH₂CO₂ ^(i)C₃H₇ 1-1678 F Br H CF₃ H OCH₂C≡CH 1-1679 F Br H CF₃ H OCH(CH₃)C≡CH 1-1680 F Br H CF₃ H OCH(CH₃)CO₂C₂H₅ 1-1681 F Br H CF₃ CH₃ OCH₂C≡CH 1-1682 F Br H CF₃ CH₃ OCH(CH₃)C≡CH 1-1683 F Br H CF₃ CH₃ OCH(CH₃)CO₂C₂H₅ 1-1684 F Br CH₃ CF₃ H OCH₂C≡CH 1-1685 F Br CH₃ CF₃ H OCH(CH₃)C≡CH 1-1686 F Br CH₃ CF₃ H OCH(CH₃)CO₂C₂H₅ 1-1687 Cl Cl H CF₃ H H 1-1688 Cl Cl H CF₃ H OH 1-1689 Cl Cl H CF₃ H NO₂ 1-1690 Cl Cl H CF₃ H NH₂ 1-1691 Cl Cl H CF₃ H NHSO₂CH₃ 1-1692 Cl Cl H CF₃ H NHSO₂CH₂Cl 1-1693 Cl Cl H CF₃ H NHCH₂CO₂CH₃ 1-1694 Cl Cl H CF₃ H NHCH₂CO₂C₂H₅ 1-1695 Cl Cl H CF₃ H NHCH₂CO₂ ^(i)C₃H₇ 1-1696 Cl Cl H CF₃ H NHCH(CH₃)CO₂CH₃ 1-1697 Cl Cl H CF₃ H NHCH(CH₃)CO₂C₂H₅ 1-1698 Cl Cl H CF₃ H NHCH(CH₃)CO₂ ^(i)C₃H₇ 1-1699 Cl Cl H CF₃ H CO₂H 1-1700 Cl Cl H CF₃ H CO₂CH₃ 1-1701 Cl Cl H CF₃ H CO₂C₂H₅ 1-1702 Cl Cl H CF₃ H CO₂ ^(n)C₃H₇ 1-1703 Cl Cl H CF₃ H CO₂ ^(n)C₄H₉ 1-1704 Cl Cl H CF₃ H CO₂ ^(n)C₅H₁₁ 1-1705 Cl Cl H CF₃ H CO₂ ^(i)C₃H₇ 1-1706 Cl Cl H CF₃ H CO₂CH₂CH₂Cl 1-1707 Cl Cl H CF₃ H CO₂CH₂CH₂Br 1-1708 Cl Cl H CF₃ H CON(CH₃)₂ 1-1709 Cl Cl H CF₃ H CONHCH₃ 1-1710 Cl Cl H CF₃ H CON(C₂H₅)₂ 1-1711 Cl Cl H CF₃ H CONHC₂H₅ 1-1712 Cl Cl H CF₃ H COCH₃ 1-1713 Cl Cl H CF₃ H COC₂H₅ 1-1714 Cl Cl H CF₃ H COCH₂Cl 1-1715 Cl Cl H CF₃ H CHO 1-1716 Cl Cl H CF₃ H CH═CHCO₂CH₃ 1-1717 Cl Cl H CF₃ H O^(i)C₃H₇ 1-1718 Cl Cl H CF₃ CH₃ H 1-1719 Cl Cl H CF₃ CH₃ OH 1-1720 Cl Cl H CF₃ CH₃ NO₂ 1-1721 Cl Cl H CF₃ CH₃ NH₂ 1-1722 Cl Cl H CF₃ CH₃ NHSO₂CH₃ 1-1723 Cl Cl H CF₃ CH₃ NHSO₂CH₂Cl 1-1724 Cl Cl H CF₃ CH₃ NHCH₂CO₂CH₃ 1-1725 Cl Cl H CF₃ CH₃ NHCH₂CO₂C₂H₅ 1-1726 Cl Cl H CF₃ CH₃ NHCH₂CO₂ ^(i)C₃H₇ 1-1727 Cl Cl H CF₃ CH₃ NHCH(CH₃)CO₂CH₃ 1-1728 Cl Cl H CF₃ CH₃ NHCH(CH₃)CO₂C₂H₅ 1-1729 Cl Cl H CF₃ CH₃ NHCH(CH₃)CO₂ ^(i)C₃H₇ 1-1730 Cl Cl H CF₃ CH₃ CO₂H 1-1731 Cl Cl H CF₃ CH₃ CO₂CH₃ 1-1732 Cl Cl H CF₃ CH₃ CO₂C₂H₅ 1-1733 Cl Cl H CF₃ CH₃ CO₂ ^(n)C₃H₇ 1-1734 Cl Cl H CF₃ CH₃ CO₂ ^(n)C₄H₉ 1-1735 Cl Cl H CF₃ CH₃ CO₂ ^(n)C₅H₁₁ 1-1736 Cl Cl H CF₃ CH₃ CO₂ ^(i)C₃H₇ 1-1737 Cl Cl H CF₃ CH₃ CO₂CH₂CH₂Cl 1-1738 Cl Cl H CF₃ CH₃ CO₂CH₂CH₂Br 1-1739 Cl Cl H CF₃ CH₃ CON(CH₃)₂ 1-1740 Cl Cl H CF₃ CH₃ CONHCH₃ 1-1741 Cl Cl H CF₃ CH₃ CON(C₂H₅)₂ 1-1742 Cl Cl H CF₃ CH₃ CONHC₂H₅ 1-1743 Cl Cl H CF₃ CH₃ COCH₃ 1-1744 Cl Cl H CF₃ CH₃ COC₂H₅ 1-1745 Cl Cl H CF₃ CH₃ COCH₂Cl 1-1746 Cl Cl H CF₃ CH₃ CHO 1-1747 Cl Cl H CF₃ CH₃ CH═CHCO₂CH₃ 1-1748 Cl Cl H CF₃ CH₃ O^(i)C₃H₇ 1-1749 Cl Cl CH₃ CF₃ H H 1-1750 Cl Cl CH₃ CF₃ H OH 1-1751 Cl Cl CH₃ CF₃ H NO₂ 1-1752 Cl Cl CH₃ CF₃ H NH₂ 1-1753 Cl Cl CH₃ CF₃ H NHSO₂CH₃ 1-1754 Cl Cl CH₃ CF₃ H NHSO₂CH₂Cl 1-1755 Cl Cl CH₃ CF₃ H NHCH₂CO₂CH₃ 1-1756 Cl Cl CH₃ CF₃ H NHCH₂CO₂C₂H₅ 1-1757 Cl Cl CH₃ CF₃ H NHCH₂CO₂ ^(i)C₃H₇ 1-1758 Cl Cl CH₃ CF₃ H NHCH(CH₃)CO₂CH₃ 1-1759 Cl Cl CH₃ CF₃ H NHCH(CH₃)CO₂C₂H₅ 1-1760 Cl Cl CH₃ CF₃ H NHCH(CH₃)CO₂ ^(i)C₃H₇ 1-1761 Cl Cl CH₃ CF₃ H CO₂H 1-1762 Cl Cl CH₃ CF₃ H CO₂CH₃ 1-1763 Cl Cl CH₃ CF₃ H CO₂C₂H₅ 1-1764 Cl Cl CH₃ CF₃ H CO₂ ^(n)C₃H₇ 1-1765 Cl Cl CH₃ CF₃ H CO₂ ^(n)C₄H₉ 1-1766 Cl Cl CH₃ CF₃ H CO₂ ^(n)C₅H₁₁ 1-1767 Cl Cl CH₃ CF₃ H CO₂ ^(i)C₃H₇ 1-1768 Cl Cl CH₃ CF₃ H CO₂CH₂CH₂Cl 1-1769 Cl Cl CH₃ CF₃ H CO₂CH₂CH₂Br 1-1770 Cl Cl CH₃ CF₃ H CON(CH₃)₂ 1-1771 Cl Cl CH₃ CF₃ H CONHCH₃ 1-1772 Cl Cl CH₃ CF₃ H CON(C₂H₅)₂ 1-1773 Cl Cl CH₃ CF₃ H CONHC₂H₅ 1-1774 Cl Cl CH₃ CF₃ H COCH₃ 1-1775 Cl Cl CH₃ CF₃ H COC₂H₅ 1-1776 Cl Cl CH₃ CF₃ H COCH₂Cl 1-1777 Cl Cl CH₃ CF₃ H CHO 1-1778 Cl Cl CH₃ CF₃ H CH═CHCO₂CH₃ 1-1779 Cl Cl CH₃ CF₃ H O^(i)C₃H₇ 1-1780 F Br H CF₃ H O^(i)C₃H₇ 1-1781 F Br H CF₃ H N(SO₂CH₃)₂ 1-1782 F Br H CF₃ H NHSO₂CH₃ 1-1783 F Br H CF₃ CH₃ O^(i)C₃H₇ 1-1784 F Br H CF₃ CH₃ N(SO₂CH₃)₂ 1-1785 F Br H CF₃ CH₃ NHSO₂CH₃ 1-1786 F Br CH₃ CF₃ H O^(i)C₃H₇ 1-1787 F Br CH₃ CF₃ H N(SO₂CH₃)₂ 1-1788 F Br CH₃ CF₃ H NHSO₂CH₃ 1-1789 F Cl H CF₃ CH₃ OCH₂C(CH₃)═CH₂ 1-1790 F Cl H CF₃ CH₃ OCH₂CO₂C₇H₁₅ 1-1791 F Cl H CF₃ CH₃ OCH₂CO₂C₈H₁₇ 1-1792 F Cl H CF₃ CH₃ COOCH₂C₆H₅ 1-1793 F Cl H CF₃ CH₃ C(CH₃)═NOH 1-1794 F Cl H CF₃ CH₃ C(CH₃)═NOCH₃ 1-1795 F Cl H CF₃ CH₃ C(CH₃)═NOC₂H₅ 1-1796 F Cl H CF₃ CH₃ C(CH₃)═NO^(i)C₃H₇ 1-1797 F Cl H CF₃ CH₃ C(C₂H₅)═NOH 1-1798 F Cl H CF₃ CH₃ C(C₂H₅)═NOCH₃ 1-1799 F Cl H CF₃ CH₃ C(C₂H₅)═NOC₂H₅ 1-1800 F Cl H CF₃ CH₃ C(C₂H₅)═NO^(i)C₃H₇ 1-1801 F Cl H CF₃ CH₃ C(CH₃)═NNH₂ 1-1802 F Cl H CF₃ CH₃ C(CH₃)═NNHCH₃ 1-1803 F Cl H CF₃ CH₃ C(CH₃)═NN(CH₃)₂ 1-1804 F Cl H CF₃ CH₃ C(CH₃)═NNHC₂H₅ 1-1805 F Cl H CF₃ CH₃ C(CH₃)═NN(C₂H₅)₂ 1-1806 F Cl H CF₃ CH₃ C(C₂H₅)═NNH₂ 1-1807 F Cl H CF₃ CH₃ C(C₂H₅)═NNHCH₃ 1-1808 F Cl H CF₃ CH₃ C(C₂H₅)═NN(CH₃)₂ 1-1809 F Cl H CF₃ CH₃ C(C₂H₅)═NNHC₂H₅ 1-1810 F Cl H CF₃ CH₃ C(C₂H₅)═NN(C₂H₅)₂ 1-1811 F Cl H CF₃ CH₃ C(CH₃)(OCH₃)₂ 1-1812 F Cl H CF₃ CH₃ C(CH₃)(OC₂H₅)₂ 1-1813 F Cl H CF₃ CH₃ C(CH₃)(C^(i)C₃H₇)₂ 1-1814 F Cl H CF₃ CH₃

1-1815 F Cl H CF₃ CH₃

1-1816 F Cl H CF₃ CH₃

1-1817 F Cl H CF₃ CH₃

1-1818 F Cl H CF₃ H OCH₂C(CH₃)═CH₂ 1-1819 F Cl H CF₃ H OCH₂CO₂C₇H₁₅ 1-1820 F Cl H CF₃ H OCH₂CO₂C₈H₁₇ 1-1821 F Cl H CF₃ H COOCH₂C₆H₅ 1-1822 F Cl H CF₃ H C(CH₃)═NOH 1-1823 F Cl H CF₃ H C(CH₃)═NOCH₃ 1-1824 F Cl H CF₃ H C(CH₃)═NOC₂H₅ 1-1825 F Cl H CF₃ H C(CH₃)═NO^(i)C₃H₇ 1-1826 F Cl H CF₃ H C(C₂H₅)═NOH 1-1827 F Cl H CF₃ H C(C₂H₅)═NOCH₃ 1-1828 F Cl H CF₃ H C(C₂H₅)═NOC₂H₅ 1-1829 F Cl H CF₃ H C(C₂H₅)═NO^(i)C₃H₇ 1-1830 F Cl H CF₃ H C(CH₃)═NNH₂ 1-1831 F Cl H CF₃ H C(CH₃)═NNHCH₃ 1-1832 F Cl H CF₃ H C(CH₃)═NN(CH₃)₂ 1-1833 F Cl H CF₃ H C(CH₃)═NNHC₂H₅ 1-1834 F Cl H CF₃ H C(CH₃)═NN(C₂H₅)₂ 1-1835 F Cl H CF₃ H C(C₂H₅)═NNH₂ 1-1836 F Cl H CF₃ H C(C₂H₅)═NNHCH₃ 1-1837 F Cl H CF₃ H C(C₂H₅)═NN(CH₃)₂ 1-1838 F Cl H CF₃ H C(C₂H₅)═NNHC₂H₅ 1-1839 F Cl H CF₃ H C(C₂H₅)═NN(C₂H₅)₂ 1-1840 F Cl H CF₃ H C(CH₃)(OCH₃)₂ 1-1841 F Cl H CF₃ H C(CH₃)(OC₂H₅)₂ 1-1842 F Cl H CF₃ H C(CH₃)(C^(i)C₃H₇)₂ 1-1843 F Cl H CF₃ H

1-1844 F Cl H CF₃ H

1-1845 F Cl H CF₃ H

1-1846 F Cl H CF₃ H

1-1847 F Cl CH₃ CF₃ H OCH₂C(CH₃)═CH₂ 1-1848 F Cl CH₃ CF₃ H OCH₂CO₂C₇H₁₅ 1-1849 F Cl CH₃ CF₃ H OCH₂CO₂C₈H₁₇ 1-1850 F Cl CH₃ CF₃ H COOCH₂C₆H₅ 1-1851 F Cl CH₃ CF₃ H C(CH₃)═NOH 1-1852 F Cl CH₃ CF₃ H C(CH₃)═NOCH₃ 1-1853 F Cl CH₃ CF₃ H C(CH₃)═NOC₂H₅ 1-1854 F Cl CH₃ CF₃ H C(CH₃)═NO^(i)C₃H₇ 1-1855 F Cl CH₃ CF₃ H C(C₂H₅)═NOH 1-1856 F Cl CH₃ CF₃ H C(C₂H₅)═NOCH₃ 1-1857 F Cl CH₃ CF₃ H C(C₂H₅)═NOC₂H₅ 1-1858 F Cl CH₃ CF₃ H C(C₂H₅)═NO^(i)C₃H₇ 1-1859 F Cl CH₃ CF₃ H C(CH₃)═NNH₂ 1-1860 F Cl CH₃ CF₃ H C(CH₃)═NNHCH₃ 1-1861 F Cl CH₃ CF₃ H C(CH₃)═NN(CH₃)₂ 1-1862 F Cl CH₃ CF₃ H C(CH₃)═NNHC₂H₅ 1-1863 F Cl CH₃ CF₃ H C(CH₃)═NN(C₂H₅)₂ 1-1864 F Cl CH₃ CF₃ H C(C₂H₅)═NNH₂ 1-1865 F Cl CH₃ CF₃ H C(C₂H₅)═NNHCH₃ 1-1866 F Cl CH₃ CF₃ H C(C₂H₅)═NN(CH₃)₂ 1-1867 F Cl CH₃ CF₃ H C(C₂H₅)═NNHC₂H₅ 1-1868 F Cl CH₃ CF₃ H C(C₂H₅)═NN(C₂H₅)₂ 1-1869 F Cl CH₃ CF₃ H C(CH₃)(OCH₃)₂ 1-1870 F Cl CH₃ CF₃ H C(CH₃)(OC₂H₅)₂ 1-1871 F Cl CH₃ CF₃ H C(CH₃)(C^(i)C₃H₇)₂ 1-1872 F Cl CH₃ CF₃ H

1-1873 F Cl CH₃ CF₃ H

1-1874 F Cl CH₃ CF₃ H

1-1875 F Cl CH₃ CF₃ H

1-1876 H Cl H CF₃ CH₃ OCH₂C(CH₃)═CH₂ 1-1877 H Cl H CF₃ CH₃ OCH₂CO₂C₇H₁₅ 1-1878 H Cl H CF₃ CH₃ OCH₂CO₂C₈H₁₇ 1-1879 H Cl H CF₃ CH₃ COOCH₂C₆H₅ 1-1880 H Cl H CF₃ CH₃ C(CH₃)═NOH 1-1881 H Cl H CF₃ CH₃ C(CH₃)═NOCH₃ 1-1882 H Cl H CF₃ CH₃ C(CH₃)═NOC₂H₅ 1-1883 H Cl H CF₃ CH₃ C(CH₃)═NO^(i)C₃H₇ 1-1884 H Cl H CF₃ CH₃ C(C₂H₅)═NOH 1-1885 H Cl H CF₃ CH₃ C(C₂H₅)═NOCH₃ 1-1886 H Cl H CF₃ CH₃ C(C₂H₅)═NOC₂H₅ 1-1887 H Cl H CF₃ CH₃ C(C₂H₅)═NO^(i)C₃H₇ 1-1888 H Cl H CF₃ CH₃ C(CH₃)═NNH₂ 1-1889 H Cl H CF₃ CH₃ C(CH₃)═NNHCH₃ 1-1890 H Cl H CF₃ CH₃ C(CH₃)═NN(CH₃)₂ 1-1891 H Cl H CF₃ CH₃ C(CH₃)═NNHC₂H₅ 1-1892 H Cl H CF₃ CH₃ C(CH₃)═NN(C₂H₅)₂ 1-1893 H Cl H CF₃ CH₃ C(C₂H₅)═NNH₂ 1-1894 H Cl H CF₃ CH₃ C(C₂H₅)═NNHCH₃ 1-1895 H Cl H CF₃ CH₃ C(C₂H₅)═NN(CH₃)₂ 1-1896 H Cl H CF₃ CH₃ C(C₂H₅)═NNHC₂H₅ 1-1897 H Cl H CF₃ CH₃ C(C₂H₅)═NN(C₂H₅)₂ 1-1898 H Cl H CF₃ CH₃ C(CH₃)(OCH₃)₂ 1-1899 H Cl H CF₃ CH₃ C(CH₃)(OC₂H₅)₂ 1-1900 H Cl H CF₃ CH₃ C(CH₃)(C^(i)C₃H₇)₂ 1-1901 H Cl H CF₃ CH₃

1-1902 H Cl H CF₃ CH₃

1-1903 H Cl H CF₃ CH₃

1-1904 H Cl H CF₃ CH₃

1-1905 H Cl H CF₃ H OCH₂C(CH₃)═CH₂ 1-1906 H Cl H CF₃ H OCH₂CO₂C₇H₁₅ 1-1907 H Cl H CF₃ H OCH₂CO₂C₈H₁₇ 1-1908 H Cl H CF₃ H COOCH₂C₆H₅ 1-1909 H Cl H CF₃ H C(CH₃)═NOH 1-1910 H Cl H CF₃ H C(CH₃)═NOCH₃ 1-1911 H Cl H CF₃ H C(CH₃)═NOC₂H₅ 1-1912 H Cl H CF₃ H C(CH₃)═NO^(i)C₃H₇ 1-1913 H Cl H CF₃ H C(C₂H₅)═NOH 1-1914 H Cl H CF₃ H C(C₂H₅)═NOCH₃ 1-1915 H Cl H CF₃ H C(C₂H₅)═NOC₂H₅ 1-1916 H Cl H CF₃ H C(C₂H₅)═NO^(i)C₃H₇ 1-1917 H Cl H CF₃ H C(CH₃)═NNH₂ 1-1918 H Cl H CF₃ H C(CH₃)═NNHCH₃ 1-1919 H Cl H CF₃ H C(CH₃)═NN(CH₃)₂ 1-1920 H Cl H CF₃ H C(CH₃)═NNHC₂H₅ 1-1921 H Cl H CF₃ H C(CH₃)═NN(C₂H₅)₂ 1-1922 H Cl H CF₃ H C(C₂H₅)═NNH₂ 1-1923 H Cl H CF₃ H C(C₂H₅)═NNHCH₃ 1-1924 H Cl H CF₃ H C(C₂H₅)═NN(CH₃)₂ 1-1925 H Cl H CF₃ H C(C₂H₅)═NNHC₂H₅ 1-1926 H Cl H CF₃ H C(C₂H₅)═NN(C₂H₅)₂ 1-1927 H Cl H CF₃ H C(CH₃)(OCH₃)₂ 1-1928 H Cl H CF₃ H C(CH₃)(OC₂H₅)₂ 1-1929 H Cl H CF₃ H C(CH₃)(C^(i)C₃H₇)₂ 1-1930 H Cl H CF₃ H

1-1931 H Cl H CF₃ H

1-1932 H Cl H CF₃ H

1-1933 H Cl H CF₃ H

1-1934 H Cl CH₃ CF₃ H OCH₂C(CH₃)═CH₂ 1-1935 H Cl CH₃ CF₃ H OCH₂CO₂C₇H₁₅ 1-1936 H Cl CH₃ CF₃ H OCH₂CO₂C₈H₁₇ 1-1937 H Cl CH₃ CF₃ H COOCH₂C₆H₅ 1-1938 H Cl CH₃ CF₃ H C(CH₃)═NOH 1-1939 H Cl CH₃ CF₃ H C(CH₃)═NOCH₃ 1-1940 H Cl CH₃ CF₃ H C(CH₃)═NOC₂H₅ 1-1941 H Cl CH₃ CF₃ H C(CH₃)═NO^(i)C₃H₇ 1-1942 H Cl CH₃ CF₃ H C(C₂H₅)═NOH 1-1943 H Cl CH₃ CF₃ H C(C₂H₅)═NOCH₃ 1-1944 H Cl CH₃ CF₃ H C(C₂H₅)═NOC₂H₅ 1-1945 H Cl CH₃ CF₃ H C(C₂H₅)═NO^(i)C₃H₇ 1-1946 H Cl CH₃ CF₃ H C(CH₃)═NNH₂ 1-1947 H Cl CH₃ CF₃ H C(CH₃)═NNHCH₃ 1-1948 H Cl CH₃ CF₃ H C(CH₃)═NN(CH₃)₂ 1-1949 H Cl CH₃ CF₃ H C(CH₃)═NNHC₂H₅ 1-1950 H Cl CH₃ CF₃ H C(CH₃)═NN(C₂H₅)₂ 1-1951 H Cl CH₃ CF₃ H C(C₂H₅)═NNH₂ 1-1952 H Cl CH₃ CF₃ H C(C₂H₅)═NNHCH₃ 1-1953 H Cl CH₃ CF₃ H C(C₂H₅)═NN(CH₃)₂ 1-1954 H Cl CH₃ CF₃ H C(C₂H₅)═NNHC₂H₅ 1-1955 H Cl CH₃ CF₃ H C(C₂H₅)═NN(C₂H₅)₂ 1-1956 H Cl CH₃ CF₃ H C(CH₃)(OCH₃)₂ 1-1957 H Cl CH₃ CF₃ H C(CH₃)(OC₂H₅)₂ 1-1958 H Cl CH₃ CF₃ H C(CH₃)(C^(i)C₃H₇)₂ 1-1959 H Cl CH₃ CF₃ H

1-1960 H Cl CH₃ CF₃ H

1-1961 H Cl CH₃ CF₃ H

1-1962 H Cl CH₃ CF₃ H

1-1963 Cl Cl H CF₃ CH₃ OCH₂C(CH₃)═CH₂ 1-1964 Cl Cl H CF₃ CH₃ OCH₂CO₂C₇H₁₅ 1-1965 Cl Cl H CF₃ CH₃ OCH₂CO₂C₈H₁₇ 1-1966 Cl Cl H CF₃ CH₃ COOCH₂C₆H₅ 1-1967 Cl Cl H CF₃ CH₃ C(CH₃)═NOH 1-1968 Cl Cl H CF₃ CH₃ C(CH₃)═NOCH₃ 1-1969 Cl Cl H CF₃ CH₃ C(CH₃)═NOC₂H₅ 1-1970 Cl Cl H CF₃ CH₃ C(CH₃)═NO^(i)C₃H₇ 1-1971 Cl Cl H CF₃ CH₃ C(C₂H₅)═NOH 1-1972 Cl Cl H CF₃ CH₃ C(C₂H₅)═NOCH₃ 1-1973 Cl Cl H CF₃ CH₃ C(C₂H₅)═NOC₂H₅ 1-1974 Cl Cl H CF₃ CH₃ C(C₂H₅)═NO^(i)C₃H₇ 1-1975 Cl Cl H CF₃ CH₃ C(CH₃)═NNH₂ 1-1976 Cl Cl H CF₃ CH₃ C(CH₃)═NNHCH₃ 1-1977 Cl Cl H CF₃ CH₃ C(CH₃)═NN(CH₃)₂ 1-1978 Cl Cl H CF₃ CH₃ C(CH₃)═NNHC₂H₅ 1-1979 Cl Cl H CF₃ CH₃ C(CH₃)═NN(C₂H₅)₂ 1-1980 Cl Cl H CF₃ CH₃ C(C₂H₅)═NNH₂ 1-1981 Cl Cl H CF₃ CH₃ C(C₂H₅)═NNHCH₃ 1-1982 Cl Cl H CF₃ CH₃ C(C₂H₅)═NN(CH₃)₂ 1-1983 Cl Cl H CF₃ CH₃ C(C₂H₅)═NNHC₂H₅ 1-1984 Cl Cl H CF₃ CH₃ C(C₂H₅)═NN(C₂H₅)₂ 1-1985 Cl Cl H CF₃ CH₃ C(CH₃)(OCH₃)₂ 1-1986 Cl Cl H CF₃ CH₃ C(CH₃)(OC₂H₅)₂ 1-1987 Cl Cl H CF₃ CH₃ C(CH₃)(C^(i)C₃H₇)₂ 1-1988 Cl Cl H CF₃ CH₃

1-1989 Cl Cl H CF₃ CH₃

1-1990 Cl Cl H CF₃ CH₃

1-1991 Cl Cl H CF₃ CH₃

1-1992 Cl Cl H CF₃ H OCH₂C(CH₃)═CH₂ 1-1993 Cl Cl H CF₃ H OCH₂CO₂C₇H₁₅ 1-1994 Cl Cl H CF₃ H OCH₂CO₂C₈H₁₇ 1-1995 Cl Cl H CF₃ H COOCH₂C₆H₅ 1-1996 Cl Cl H CF₃ H C(CH₃)═NOH 1-1997 Cl Cl H CF₃ H C(CH₃)═NOCH₃ 1-1998 Cl Cl H CF₃ H C(CH₃)═NOC₂H₅ 1-1999 Cl Cl H CF₃ H C(CH₃)═NO^(i)C₃H₇ 1-2000 Cl Cl H CF₃ H C(C₂H₅)═NOH 1-2001 Cl Cl H CF₃ H C(C₂H₅)═NOCH₃ 1-2002 Cl Cl H CF₃ H C(C₂H₅)═NOC₂H₅ 1-2003 Cl Cl H CF₃ H C(C₂H₅)═NO^(i)C₃H₇ 1-2004 Cl Cl H CF₃ H C(CH₃)═NNH₂ 1-2005 Cl Cl H CF₃ H C(CH₃)═NNHCH₃ 1-2006 Cl Cl H CF₃ H C(CH₃)═NN(CH₃)₂ 1-2007 Cl Cl H CF₃ H C(CH₃)═NNHC₂H₅ 1-2008 Cl Cl H CF₃ H C(CH₃)═NN(C₂H₅)₂ 1-2009 Cl Cl H CF₃ H C(C₂H₅)═NNH₂ 1-2010 Cl Cl H CF₃ H C(C₂H₅)═NNHCH₃ 1-2011 Cl Cl H CF₃ H C(C₂H₅)═NN(CH₃)₂ 1-2012 Cl Cl H CF₃ H C(C₂H₅)═NNHC₂H₅ 1-2013 Cl Cl H CF₃ H C(C₂H₅)═NN(C₂H₅)₂ 1-2014 Cl Cl H CF₃ H C(CH₃)(OCH₃)₂ 1-2015 Cl Cl H CF₃ H C(CH₃)(OC₂H₅)₂ 1-2016 Cl Cl H CF₃ H C(CH₃)(C^(i)C₃H₇)₂ 1-2017 Cl Cl H CF₃ H

1-2018 Cl Cl H CF₃ H

1-2019 Cl Cl H CF₃ H

1-2020 Cl Cl H CF₃ H

1-2021 Cl Cl CH₃ CF₃ H OCH₂C(CH₃)═CH₂ 1-2022 Cl Cl CH₃ CF₃ H OCH₂CO₂C₇H₁₅ 1-2023 Cl Cl CH₃ CF₃ H OCH₂CO₂C₈H₁₇ 1-2024 Cl Cl CH₃ CF₃ H COOCH₂C₆H₅ 1-2025 Cl Cl CH₃ CF₃ H C(CH₃)═NOH 1-2026 Cl Cl CH₃ CF₃ H C(CH₃)═NOCH₃ 1-2027 Cl Cl CH₃ CF₃ H C(CH₃)═NOC₂H₅ 1-2028 Cl Cl CH₃ CF₃ H C(CH₃)═NO^(i)C₃H₇ 1-2029 Cl Cl CH₃ CF₃ H C(C₂H₅)═NOH 1-2030 Cl Cl CH₃ CF₃ H C(C₂H₅)═NOCH₃ 1-2031 Cl Cl CH₃ CF₃ H C(C₂H₅)═NOC₂H₅ 1-2032 Cl Cl CH₃ CF₃ H C(C₂H₅)═NO^(i)C₃H₇ 1-2033 Cl Cl CH₃ CF₃ H C(CH₃)═NNH₂ 1-2034 Cl Cl CH₃ CF₃ H C(CH₃)═NNHCH₃ 1-2035 Cl Cl CH₃ CF₃ H C(CH₃)═NN(CH₃)₂ 1-2036 Cl Cl CH₃ CF₃ H C(CH₃)═NNHC₂H₅ 1-2037 Cl Cl CH₃ CF₃ H C(CH₃)═NN(C₂H₅)₂ 1-2038 Cl Cl CH₃ CF₃ H C(C₂H₅)═NNH₂ 1-2039 Cl Cl CH₃ CF₃ H C(C₂H₅)═NNHCH₃ 1-2040 Cl Cl CH₃ CF₃ H C(C₂H₅)═NN(CH₃)₂ 1-2041 Cl Cl CH₃ CF₃ H C(C₂H₅)═NNHC₂H₅ 1-2042 Cl Cl CH₃ CF₃ H C(C₂H₅)═NN(C₂H₅)₂ 1-2043 Cl Cl CH₃ CF₃ H C(CH₃)(OCH₃)₂ 1-2044 Cl Cl CH₃ CF₃ H C(CH₃)(OC₂H₅)₂ 1-2045 Cl Cl CH₃ CF₃ H C(CH₃)(C^(i)C₃H₇)₂ 1-2046 Cl Cl CH₃ CF₃ H

1-2047 Cl Cl CH₃ CF₃ H

1-2048 Cl Cl CH₃ CF₃ H

1-2049 Cl Cl CH₃ CF₃ H

1-2050 F Cl H CF₃ CH₃ OCH₂COOCH₂COOCH₃ 1-2051 F Cl H CF₃ CH₃ OCH₂COOCH₂COOC₂H₅ 1-2052 F Cl H CF₃ CH₃ OCH₂COOCH₂COO^(i)C₃H₇ 1-2053 F Cl H CF₃ CH₃ OCH₂COOCH(CH₃)COOCH₃ 1-2054 F Cl H CF₃ CH₃ OCH₂COOCH(CH₃)COOC₂H₅ 1-2055 F Cl H CF₃ CH₃ OCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2056 F Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COOCH₃ 1-2057 F Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COOC₂H₅ 1-2058 F Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2059 F Cl H CF₃ CH₃ OCH(CH₃)COOCH(CH₃)COOCH₃ 1-2060 F Cl H CF₃ CH₃ OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2061 F Cl H CF₃ CH₃ OCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2062 F Cl H CF₃ H OCH₂COOCH₂COOCH₃ 1-2063 F Cl H CF₃ H OCH₂COOCH₂COOC₂H₅ 1-2064 F Cl H CF₃ H OCH₂COOCH₂COO^(i)C₃H₇ 1-2065 F Cl H CF₃ H OCH₂COOCH(CH₃)COOCH₃ 1-2066 F Cl H CF₃ H OCH₂COOCH(CH₃)COOC₂H₅ 1-2067 F Cl H CF₃ H OCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2068 F Cl H CF₃ H OCH(CH₃)COOCH₂COOCH₃ 1-2069 F Cl H CF₃ H OCH(CH₃)COOCH₂COOC₂H₅ 1-2070 F Cl H CF₃ H OCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2071 F Cl H CF₃ H OCH(CH₃)COOCH(CH₃)COOCH₃ 1-2072 F Cl H CF₃ H OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2073 F Cl H CF₃ H OCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2074 F Cl CH₃ CF₃ H OCH₂COOCH₂COOCH₃ 1-2075 F Cl CH₃ CF₃ H OCH₂COOCH₂COOC₂H₅ 1-2076 F Cl CH₃ CF₃ H OCH₂COOCH₂COO^(i)C₃H₇ 1-2077 F Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COOCH₃ 1-2078 F Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COOC₂H₅ 1-2079 F Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2080 F Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COOCH₃ 1-2081 F Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COOC₂H₅ 1-2082 F Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2083 F Cl CH₃ CF₃ H OCH(CH₃)COOCH(CH₃)COOCH₃ 1-2084 F Cl CH₃ CF₃ H OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2085 F Cl CH₃ CF₃ H OCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2086 H Cl H CF₃ CH₃ OCH₂COOCH₂COOCH₃ 1-2087 H Cl H CF₃ CH₃ OCH₂COOCH₂COOC₂H₅ 1-2088 H Cl H CF₃ CH₃ OCH₂COOCH₂COO^(i)C₃H₇ 1-2089 H Cl H CF₃ CH₃ OCH₂COOCH(CH₃)COOCH₃ 1-2090 H Cl H CF₃ CH₃ OCH₂COOCH(CH₃)COOC₂H₅ 1-2091 H Cl H CF₃ CH₃ OCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2092 H Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COOCH₃ 1-2093 H Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COOC₂H₅ 1-2094 H Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2095 H Cl H CF₃ CH₃ OCH(CH₃)COOCH(CH₃)COOCH₃ 1-2096 H Cl H CF₃ CH₃ OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2097 H Cl H CF₃ CH₃ OCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2098 H Cl H CF₃ H OCH₂COOCH₂COOCH₃ 1-2099 H Cl H CF₃ H OCH₂COOCH₂COOC₂H₅ 1-2100 H Cl H CF₃ H OCH₂COOCH₂COO^(i)C₃H₇ 1-2101 H Cl H CF₃ H OCH₂COOCH(CH₃)COOCH₃ 1-2102 H Cl H CF₃ H OCH₂COOCH(CH₃)COOC₂H₅ 1-2103 H Cl H CF₃ H OCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2104 H Cl H CF₃ H OCH(CH₃)COOCH₂COOCH₃ 1-2105 H Cl H CF₃ H OCH(CH₃)COOCH₂COOC₂H₅ 1-2106 H Cl H CF₃ H OCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2107 H Cl H CF₃ H OCH(CH₃)COOCH(CH₃)COOCH₃ 1-2108 H Cl H CF₃ H OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2109 H Cl H CF₃ H OCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2110 H Cl CH₃ CF₃ H OCH₂COOCH₂COOCH₃ 1-2111 H Cl CH₃ CF₃ H OCH₂COOCH₂COOC₂H₅ 1-2112 H Cl CH₃ CF₃ H OCH₂COOCH₂COO^(i)C₃H₇ 1-2113 H Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COOCH₃ 1-2114 H Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COOC₂H₅ 1-2115 H Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2116 H Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COOCH₃ 1-2117 H Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COOC₂H₅ 1-2118 H Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2119 H Cl CH₃ CF₃ H OCH(CH₃)COOCH(CH₃)COOCH₃ 1-2120 H Cl CH₃ CF₃ H OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2121 H Cl CH₃ CF₃ H OCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2122 Cl Cl H CF₃ CH₃ OCH₂COOCH₂COOCH₃ 1-2123 Cl Cl H CF₃ CH₃ OCH₂COOCH₂COOC₂H₅ 1-2124 Cl Cl H CF₃ CH₃ OCH₂COOCH₂COO^(i)C₃H₇ 1-2125 Cl Cl H CF₃ CH₃ OCH₂COOCH(CH₃)COOCH₃ 1-2126 Cl Cl H CF₃ CH₃ OCH₂COOCH(CH₃)COOC₂H₅ 1-2127 Cl Cl H CF₃ CH₃ OCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2128 Cl Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COOCH₃ 1-2129 Cl Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COOC₂H₅ 1-2130 Cl Cl H CF₃ CH₃ OCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2131 Cl Cl H CF₃ CH₃ OCH(CH₃)COOCH(CH₃)COOCH₃ 1-2132 Cl Cl H CF₃ CH₃ OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2133 Cl Cl H CF₃ CH₃ OCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2134 Cl Cl H CF₃ H OCH₂COOCH₂COOCH₃ 1-2135 Cl Cl H CF₃ H OCH₂COOCH₂COOC₂H₅ 1-2136 Cl Cl H CF₃ H OCH₂COOCH₂COO^(i)C₃H₇ 1-2137 Cl Cl H CF₃ H OCH₂COOCH(CH₃)COOCH₃ 1-2138 Cl Cl H CF₃ H OCH₂COOCH(CH₃)COOC₂H₅ 1-2139 Cl Cl H CF₃ H OCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2140 Cl Cl H CF₃ H OCH(CH₃)COOCH₂COOCH₃ 1-2141 Cl Cl H CF₃ H OCH(CH₃)COOCH₂COOC₂H₅ 1-2142 Cl Cl H CF₃ H OCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2143 Cl Cl H CF₃ H OCH(CH₃)COOCH(CH₃)COOCH₃ 1-2144 Cl Cl H CF₃ H OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2145 Cl Cl H CF₃ H OCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇ 1-2146 Cl Cl CH₃ CF₃ H OCH₂COOCH₂COOCH₃ 1-2147 Cl Cl CH₃ CF₃ H OCH₂COOCH₂COOC₂H₅ 1-2148 Cl Cl CH₃ CF₃ H OCH₂COOCH₂COO^(i)C₃H₇ 1-2149 Cl Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COOCH₃ 1-2150 Cl Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COOC₂H₅ 1-2151 Cl Cl CH₃ CF₃ H OCH₂COOCH(CH₃)COO^(i)C₃H₇ 1-2152 Cl Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COOCH₃ 1-2153 Cl Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COOC₂H₅ 1-2154 Cl Cl CH₃ CF₃ H OCH(CH₃)COOCH₂COO^(i)C₃H₇ 1-2155 Cl Cl CH₃ CF₃ H OCH(CH₃)COOCH(CH₃)COOCH₃ 1-2156 Cl Cl CH₃ CF₃ H OCH(CH₃)COOCH(CH₃)COOC₂H₅ 1-2157 Cl Cl CH₃ CF₃ H OCH(CH₃)COOCH(CH₃)COO^(i)C₃H₇

TABLE 2 Compounds of the formula:

Compound No. X Z¹ n R³ R¹ R² R⁴ R⁵ 2-1  H O 1 H CF₂Cl CH₃ H H 2-2  H O 1 H CF₂Cl CH₃ H CH₃ 2-3  H O 1 H CF₂Cl CH₃ H C₂H₅ 2-4  H O 1 H CF₂Cl CH₃ H ^(n)C₃H₇ 2-5  H O 1 H CF₂Cl CH₃ H ^(i)C₃H₇ 2-6  H O 1 H CF₂Cl CH₃ H ^(i)C₄H₉ 2-7  H O 1 H CF₂Cl CH₃ H ^(n)C₄H₉ 2-8  H O 1 H CF₂Cl CH₃ H CH₂CH₂Cl 2-9  H O 1 H CF₂Cl CH₃ H CH₂CH₂Br 2-10  H O 1 H CF₂Cl CH₃ H CH₂CH═CH₂ 2-11  H O 1 H CF₂Cl CH₃ H CH(CH₃)CH═CH₂ 2-12  H O 1 H CF₂Cl CH₃ H CH₂CCl═CH₂ 2-13  H O 1 H CF₂Cl CH₃ H CH₂C≡CH 2-14  H O 1 H CF₂Cl CH₃ H CH(CH₃)C≡CH 2-15  H O 1 H CF₂Cl CH₃ H CH₂CN 2-16  H O 1 H CF₂Cl CH₃ H CH₂OCH₃ 2-17  H O 1 H CF₂Cl CH₃ H CH₂OC₂H₅ 2-18  H O 1 H CF₂Cl CH₃ H CH₂COOH 2-19  H O 1 H CF₂Cl CH₃ H CH₂COOCH₃ 2-20  H O 1 H CF₂Cl CH₃ H CH₂COOC₂H₅ 2-21  H O 1 H CF₂Cl CH₃ H CH₂COO^(n)C₃H₇ 2-22  H O 1 H CF₂Cl CH₃ H CH₂COO^(n)C₄H₉ 2-23  H O 1 H CF₂Cl CH₃ H CH₂COO^(n)C₅H₁₁ 2-24  H O 1 H CF₂Cl CH₃ H CH₂COO^(i)C₃H₇ 2-25  H O 1 H CF₂Cl CH₃ H CH₂COO^(c)C₅H₉ 2-26  H O 1 H CF₂Cl CH₃ H CH₂COO^(c)C₆H₁₁ 2-27  H O 1 H CF₂Cl CH₃ H CH(CH₃)COOH 2-28  H O 1 H CF₂Cl CH₃ H CH(CH₃)COOCH₃ 2-29  H O 1 H CF₂Cl CH₃ H CH(CH₃)COOC₂H₅ 2-30  H O 1 H CF₂Cl CH₃ H CH(CH₃)COO^(n)C₃H₇ 2-31  H O 1 H CF₂Cl CH₃ H CH(CH₃)COO^(n)C₄H₉ 2-32  H O 1 H CF₂Cl CH₃ H CH(CH₃)COO^(n)C₅H₁₁ 2-33  H O 1 H CF₂Cl CH₃ H CH(CH₃)COO^(i)C₃H₇ 2-34  H O 1 H CF₂Cl CH₃ H CH(CH₃)COO^(c)C₅H₉ 2-35  H O 1 H CF₂Cl CH₃ H CH(CH₃)COO^(c)C₆H₁₁ 2-36  H O 1 H CF₂Cl CH₃ CH₃ H 2-37  H O 1 H CF₂Cl CH₃ CH₃ CH₃ 2-38  H O 1 H CF₂Cl CH₃ CH₃ C₂H₅ 2-39  H O 1 H CF₂Cl CH₃ CH₃ ^(n)C₃H₇ 2-40  H O 1 H CF₂Cl CH₃ CH₃ ^(i)C₃H₇ 2-41  H O 1 H CF₂Cl CH₃ CH₃ ^(i)C₄H₉ 2-42  H O 1 H CF₂Cl CH₃ CH₃ ^(n)C₄H₉ 2-43  H O 1 H CF₂Cl CH₃ CH₃ CH₂CH═CH₂ 2-44  H O 1 H CF₂Cl CH₃ CH₃ CH(CH₃)CH═CH₂ 2-45  H O 1 H CF₂Cl CH₃ CH₃ CH₂C≡CH 2-46  H O 1 H CF₂Cl CH₃ CH₃ CH(CH₃)C≡CH 2-47  H O 1 H CF₂Cl CH₃ CH₃ CH₂OCH₃ 2-48  H O 1 H CF₂Cl CH₃ CH₃ CH₂OC₂H₅ 2-49  F O 1 H CF₂Cl CH₃ H H 2-50  F O 1 H CF₂Cl CH₃ H CH₃ 2-51  F O 1 H CF₂Cl CH₃ H C₂H₅ 2-52  F O 1 H CF₂Cl CH₃ H ^(n)C₃H₇ 2-53  F O 1 H CF₂Cl CH₃ H ^(i)C₃H₇ 2-54  F O 1 H CF₂Cl CH₃ H ^(i)C₄H₉ 2-55  F O 1 H CF₂Cl CH₃ H ^(n)C₄H₉ 2-56  F O 1 H CF₂Cl CH₃ H CH₂CH₂Cl 2-57  F O 1 H CF₂Cl CH₃ H CH₂CH₂Br 2-58  F O 1 H CF₂Cl CH₃ H CH₂CH═CH₂ 2-59  F O 1 H CF₂Cl CH₃ H CH(CH₃)CH═CH₂ 2-60  F O 1 H CF₂Cl CH₃ H CH₂CCl═CH₂ 2-61  F O 1 H CF₂Cl CH₃ H CH₂C≡CH 2-62  F O 1 H CF₂Cl CH₃ H CH(CH₃)C≡CH 2-63  F O 1 H CF₂Cl CH₃ H CH₂CN 2-64  F O 1 H CF₂Cl CH₃ H CH₂OCH₃ 2-65  F O 1 H CF₂Cl CH₃ H CH₂OC₂H₅ 2-66  F O 1 H CF₂Cl CH₃ H CH₂COOH 2-67  F O 1 H CF₂Cl CH₃ H CH₂COOCH₃ 2-68  F O 1 H CF₂Cl CH₃ H CH₂COOC₂H₅ 2-69  F O 1 H CF₂Cl CH₃ H CH₂COO^(n)C₃H₇ 2-70  F O 1 H CF₂Cl CH₃ H CH₂COO^(n)C₄H₉ 2-71  F O 1 H CF₂Cl CH₃ H CH₂COO^(n)C₅H₁₁ 2-72  F O 1 H CF₂Cl CH₃ H CH₂COO^(i)C₃H₇ 2-73  F O 1 H CF₂Cl CH₃ H CH₂COO^(c)C₅H₉ 2-74  F O 1 H CF₂Cl CH₃ H CH₂COO^(c)C₆H₁₁ 2-75  F O 1 H CF₂Cl CH₃ H CH(CH₃)COOH 2-76  F O 1 H CF₂Cl CH₃ H CH(CH₃)COOCH₃ 2-77  F O 1 H CF₂Cl CH₃ H CH(CH₃)COOC₂H₅ 2-78  F O 1 H CF₂Cl CH₃ H CH(CH₃)COO^(n)C₃H₇ 2-79  F O 1 H CF₂Cl CH₃ H CH(CH₃)COO^(n)C₄H₉ 2-80  F O 1 H CF₂Cl CH₃ H CH(CH₃)COO^(n)C₅H₁₁ 2-81  F O 1 H CF₂Cl CH₃ H CH(CH₃)COO^(i)C₃H₇ 2-82  F O 1 H CF₂Cl CH₃ H CH(CH₃)COO^(c)C₅H₉ 2-83  F O 1 H CF₂Cl CH₃ H CH(CH₃)COO^(c)C₆H₁₁ 2-84  F O 1 H CF₂Cl CH₃ CH₃ H 2-85  F O 1 H CF₂Cl CH₃ CH₃ CH₃ 2-86  F O 1 H CF₂Cl CH₃ CH₃ C₂H₅ 2-87  F O 1 H CF₂Cl CH₃ CH₃ ^(n)C₃H₇ 2-88  F O 1 H CF₂Cl CH₃ CH₃ ^(i)C₃H₇ 2-89  F O 1 H CF₂Cl CH₃ CH₃ ^(i)C₄H₉ 2-90  F O 1 H CF₂Cl CH₃ CH₃ ^(n)C₄H₉ 2-91  F O 1 H CF₂Cl CH₃ CH₃ CH₂CH═CH₂ 2-92  F O 1 H CF₂Cl CH₃ CH₃ CH(CH₃)CH═CH₂ 2-93  F O 1 H CF₂Cl CH₃ CH₃ CH₂C≡CH 2-94  F O 1 H CF₂Cl CH₃ CH₃ CH(CH₃)C≡CH 2-95  F O 1 H CF₂Cl CH₃ CH₃ CH₂OCH₃ 2-96  F O 1 H CF₂Cl CH₃ CH₃ CH₂OC₂H₅ 2-97  H S 0 H CF₂Cl CH₃ — H 2-98  H S 0 H CF₂Cl CH₃ — CH₃ 2-99  H S 0 H CF₂Cl CH₃ — C₂H₅ 2-100 H S 0 H CF₂Cl CH₃ — ^(n)C₃H₇ 2-101 H S 0 H CF₂Cl CH₃ — ^(n)C₄H₉ 2-102 H S 0 H CF₂Cl CH₃ — ^(i)C₃H₇ 2-103 H S 0 H CF₂Cl CH₃ — ^(i)C₄H₉ 2-104 H S 0 H CF₂Cl CH₃ — CH₂CH₂Cl 2-105 H S 0 H CF₂Cl CH₃ — CH₂CH₂Br 2-106 H S 0 H CF₂Cl CH₃ — CH₂CH═CH₂ 2-107 H S 0 H CF₂Cl CH₃ — CH(CH₃)CH═CH₂ 2-108 H S 0 H CF₂Cl CH₃ — CH₂CCl═CH₂ 2-109 H S 0 H CF₂Cl CH₃ — CH₂C≡CH 2-110 H S 0 H CF₂Cl CH₃ — CH(CH₃)C≡CH 2-111 H S 0 H CF₂Cl CH₃ — CH₂CN 2-112 H S 0 H CF₂Cl CH₃ — CH₂OCH₃ 2-113 H S 0 H CF₂Cl CH₃ — CH₂OC₂H₅ 2-114 H S 0 H CF₂Cl CH₃ — CH₂COOH 2-115 H S 0 H CF₂Cl CH₃ — CH₂COOCH₃ 2-116 H S 0 H CF₂Cl CH₃ — CH₂COOC₂H₅ 2-117 H S 0 H CF₂Cl CH₃ — CH₂COO^(n)C₃H₇ 2-118 H S 0 H CF₂Cl CH₃ — CH₂COO^(n)C₄H₉ 2-119 H S 0 H CF₂Cl CH₃ — CH₂COO^(n)C₅H₁₁ 2-120 H S 0 H CF₂Cl CH₃ — CH₂COO^(i)C₃H₇ 2-121 H S 0 H CF₂Cl CH₃ — CH₂COO^(c)C₅H₉ 2-122 H S 0 H CF₂Cl CH₃ — CH₂COO^(c)C₆H₁₁ 2-123 H S 0 H CF₂Cl CH₃ — CH(CH₃)COOH 2-124 H S 0 H CF₂Cl CH₃ — CH(CH₃)COOCH₃ 2-125 H S 0 H CF₂Cl CH₃ — CH(CH₃)COOC₂H₅ 2-126 H S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(n)C₃H₇ 2-127 H S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(n)C₄H₉ 2-128 H S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(n)C₅H₁₁ 2-129 H S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(i)C₃H₇ 2-130 H S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(c)C₅H₉ 2-131 H S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(c)C₆H₁₁ 2-132 F S 0 H CF₂Cl CH₃ — H 2-133 F S 0 H CF₂Cl CH₃ — CH₃ 2-134 F S 0 H CF₂Cl CH₃ — C₂H₅ 2-135 F S 0 H CF₂Cl CH₃ — ^(n)C₃H₇ 2-136 F S 0 H CF₂Cl CH₃ — ^(n)C₄H₉ 2-137 F S 0 H CF₂Cl CH₃ — ^(i)C₃H₇ 2-138 F S 0 H CF₂Cl CH₃ — ^(i)C₄H₉ 2-139 F S 0 H CF₂Cl CH₃ — CH₂CH₂Cl 2-140 F S 0 H CF₂Cl CH₃ — CH₂CH₂Br 2-141 F S 0 H CF₂Cl CH₃ — CH₂CH═CH₂ 2-142 F S 0 H CF₂Cl CH₃ — CH(CH₃)CH═CH₂ 2-143 F S 0 H CF₂Cl CH₃ — CH₂CCl═CH₂ 2-144 F S 0 H CF₂Cl CH₃ — CH₂C≡CH 2-145 F S 0 H CF₂Cl CH₃ — CH(CH₃)C≡CH 2-146 F S 0 H CF₂Cl CH₃ — CH₂CN 2-147 F S 0 H CF₂Cl CH₃ — CH₂OCH₃ 2-148 F S 0 H CF₂Cl CH₃ — CH₂OC₂H₅ 2-149 F S 0 H CF₂Cl CH₃ — CH₂COOH 2-150 F S 0 H CF₂Cl CH₃ — CH₂COOCH₃ 2-151 F S 0 H CF₂Cl CH₃ — CH₂COOC₂H₅ 2-152 F S 0 H CF₂Cl CH₃ — CH₂COO^(n)C₃H₇ 2-153 F S 0 H CF₂Cl CH₃ — CH₂COO^(n)C₄H₉ 2-154 F S 0 H CF₂Cl CH₃ — CH₂COO^(n)C₅H₁₁ 2-155 F S 0 H CF₂Cl CH₃ — CH₂COO^(i)C₃H₇ 2-156 F S 0 H CF₂Cl CH₃ — CH₂COO^(c)C₅H₉ 2-157 F S 0 H CF₂Cl CH₃ — CH₂COO^(c)C₆H₁₁ 2-158 F S 0 H CF₂Cl CH₃ — CH(CH₃)COOH 2-159 F S 0 H CF₂Cl CH₃ — CH(CH₃)COOCH₃ 2-160 F S 0 H CF₂Cl CH₃ — CH(CH₃)COOC₂H₅ 2-161 F S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(n)C₃H₇ 2-162 F S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(n)C₄H₉ 2-163 F S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(n)C₅H₁₁ 2-164 F S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(i)C₃H₇ 2-165 F S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(c)C₅H₉ 2-166 F S 0 H CF₂Cl CH₃ — CH(CH₃)COO^(c)C₆H₁₁ 2-167 H O 0 H CF₂Cl CH₃ — H 2-168 H O 0 H CF₂Cl CH₃ — CH₃ 2-169 H O 0 H CF₂Cl CH₃ — C₂H₅ 2-170 H O 0 H CF₂Cl CH₃ — ^(n)C₃H₇ 2-171 H O 0 H CF₂Cl CH₃ — ^(n)C₄H₉ 2-172 H O 0 H CF₂Cl CH₃ — ^(i)C₃H₇ 2-173 H O 0 H CF₂Cl CH₃ — ^(i)C₄H₉ 2-174 H O 0 H CF₂Cl CH₃ — CH₂CH═CH₂ 2-175 H O 0 H CF₂Cl CH₃ — CH(CH₃)CH═CH₂ 2-176 H O 0 H CF₂Cl CH₃ — CH₂C≡CH 2-177 H O 0 H CF₂Cl CH₃ — CH(CH₃)C≡CH 2-178 H O 0 H CF₂Cl CH₃ — CH₂OCH₃ 2-179 H O 0 H CF₂Cl CH₃ — CH₂OC₂H₅ 2-180 F O 0 H CF₂Cl CH₃ — H 2-181 F O 0 H CF₂Cl CH₃ — CH₃ 2-182 F O 0 H CF₂Cl CH₃ — C₂H₅ 2-183 F O 0 H CF₂Cl CH₃ — ^(n)C₃H₇ 2-184 F O 0 H CF₂Cl CH₃ — ^(n)C₄H₉ 2-185 F O 0 H CF₂Cl CH₃ — CH₂CH═CH₂ 2-186 F O 0 H CF₂Cl CH₃ — CH(CH₃)CH═CH₂ 2-187 F O 0 H CF₂Cl CH₃ — CH₂C≡CH 2-188 F O 0 H CF₂Cl CH₃ — CH(CH₃)C≡CH 2-189 F O 0 H CF₂Cl CH₃ — CH₂OCH₃ 2-190 F O 0 H CF₂Cl CH₃ — CH₂OC₂H₅ 2-191 H O 1 H CF₃ CH₃ — H 2-192 H O 1 H CF₃ CH₃ H CH₃ 2-193 H O 1 H CF₃ CH₃ H C₂H₅ 2-194 H O 1 H CF₃ CH₃ H ^(n)C₃H₇ 2-195 H O 1 H CF₃ CH₃ H ^(i)C₃H₇ 2-196 H O 1 H CF₃ CH₃ H ^(i)C₄H₉ 2-197 H O 1 H CF₃ CH₃ H ^(n)C₄H₉ 2-198 H O 1 H CF₃ CH₃ H CH₂CH₂Cl 2-199 H O 1 H CF₃ CH₃ H CH₂CH₂Br 2-200 H O 1 H CF₃ CH₃ H CH₂CH═CH₂ 2-201 H O 1 H CF₃ CH₃ H CH(CH₃)CH═CH₂ 2-202 H O 1 H CF₃ CH₃ H CH₂CCl═CH₂ 2-203 H O 1 H CF₃ CH₃ H CH₂C≡CH 2-204 H O 1 H CF₃ CH₃ H CH(CH₃)C≡CH 2-205 H O 1 H CF₃ CH₃ H CH₂CN 2-206 H O 1 H CF₃ CH₃ H CH₂OCH₃ 2-207 H O 1 H CF₃ CH₃ H CH₂OC₂H₅ 2-208 H O 1 H CF₃ CH₃ H CH₂COOH 2-209 H O 1 H CF₃ CH₃ H CH₂COOCH₃ 2-210 H O 1 H CF₃ CH₃ H CH₂COOC₂H₅ 2-211 H O 1 H CF₃ CH₃ H CH₂COO^(n)C₃H₇ 2-212 H O 1 H CF₃ CH₃ H CH₂COO^(n)C₄H₉ 2-213 H O 1 H CF₃ CH₃ H CH₂COO^(n)C₅H₁₁ 2-214 H O 1 H CF₃ CH₃ H CH₂COO^(i)C₃H₇ 2-215 H O 1 H CF₃ CH₃ H CH₂COO^(c)C₅H₉ 2-216 H O 1 H CF₃ CH₃ H CH₂COO^(c)C₆H₁₁ 2-217 H O 1 H CF₃ CH₃ H CH(CH₃)COOH 2-218 H O 1 H CF₃ CH₃ H CH(CH₃)COOCH₃ 2-219 H O 1 H CF₃ CH₃ H CH(CH₃)COOC₂H₅ 2-220 H O 1 H CF₃ CH₃ H CH(CH₃)COO^(n)C₃H₇ 2-221 H O 1 H CF₃ CH₃ H CH(CH₃)COO^(n)C₄H₉ 2-222 H O 1 H CF₃ CH₃ H CH(CH₃)COO^(n)C₅H₁₁ 2-223 H O 1 H CF₃ CH₃ H CH(CH₃)COO^(i)C₃H₇ 2-224 H O 1 H CF₃ CH₃ H CH(CH₃)COO^(c)C₅H₉ 2-225 H O 1 H CF₃ CH₃ H CH(CH₃)COO^(c)C₆H₁₁ 2-226 H O 1 H CF₃ CH₃ CH₃ H 2-227 H O 1 H CF₃ CH₃ CH₃ CH₃ 2-228 H O 1 H CF₃ CH₃ CH₃ C₂H₅ 2-229 H O 1 H CF₃ CH₃ CH₃ ^(n)C₃H₇ 2-230 H O 1 H CF₃ CH₃ CH₃ ^(i)C₃H₇ 2-231 H O 1 H CF₃ CH₃ CH₃ ^(i)C₄H₉ 2-232 H O 1 H CF₃ CH₃ CH₃ ^(n)C₄H₉ 2-233 H O 1 H CF₃ CH₃ CH₃ CH₂CH═CH₂ 2-234 H O 1 H CF₃ CH₃ CH₃ CH(CH₃)CH═CH₂ 2-235 H O 1 H CF₃ CH₃ CH₃ CH₂C≡CH 2-236 H O 1 H CF₃ CH₃ CH₃ CH(CH₃)C≡CH 2-237 H O 1 H CF₃ CH₃ CH₃ CH₂OCH₃ 2-238 H O 1 H CF₃ CH₃ CH₃ CH₂OC₂H₅ 2-239 F O 1 H CF₃ CH₃ H H 2-240 F O 1 H CF₃ CH₃ H CH₃ 2-241 F O 1 H CF₃ CH₃ H C₂H₅ 2-242 F O 1 H CF₃ CH₃ H ^(n)C₃H₇ 2-243 F O 1 H CF₃ CH₃ H ^(i)C₃H₇ 2-244 F O 1 H CF₃ CH₃ H ^(i)C₄H₉ 2-245 F O 1 H CF₃ CH₃ H ^(n)C₄H₉ 2-246 F O 1 H CF₃ CH₃ H CH₂CH₂Cl 2-247 F O 1 H CF₃ CH₃ H CH₂CH₂Br 2-248 F O 1 H CF₃ CH₃ H CH₂CH═CH₂ 2-249 F O 1 H CF₃ CH₃ H CH(CH₃)CH═CH₂ 2-250 F O 1 H CF₃ CH₃ H CH₂CCl═CH₂ 2-251 F O 1 H CF₃ CH₃ H CH₂C≡CH 2-252 F O 1 H CF₃ CH₃ H CH(CH₃)C≡CH 2-253 F O 1 H CF₃ CH₃ H CH₂CN 2-254 F O 1 H CF₃ CH₃ H CH₂OCH₃ 2-255 F O 1 H CF₃ CH₃ H CH₂OC₂H₅ 2-256 F O 1 H CF₃ CH₃ H CH₂COOH 2-257 F O 1 H CF₃ CH₃ H CH₂COOCH₃ 2-258 F O 1 H CF₃ CH₃ H CH₂COOC₂H₅ 2-259 F O 1 H CF₃ CH₃ H CH₂COO^(n)C₃H₇ 2-260 F O 1 H CF₃ CH₃ H CH₂COO^(n)C₄H₉ 2-261 F O 1 H CF₃ CH₃ H CH₂COO^(n)C₅H₁₁ 2-262 F O 1 H CF₃ CH₃ H CH₂COO^(i)C₃H₇ 2-263 F O 1 H CF₃ CH₃ H CH₂COO^(c)C₅H₉ 2-264 F O 1 H CF₃ CH₃ H CH₂COO^(c)C₆H₁₁ 2-265 F O 1 H CF₃ CH₃ H CH(CH₃)COOH 2-266 F O 1 H CF₃ CH₃ H CH(CH₃)COOCH₃ 2-267 F O 1 H CF₃ CH₃ H CH(CH₃)COOC₂H₅ 2-268 F O 1 H CF₃ CH₃ H CH(CH₃)COO^(n)C₃H₇ 2-269 F O 1 H CF₃ CH₃ H CH(CH₃)COO^(n)C₄H₉ 2-270 F O 1 H CF₃ CH₃ H CH(CH₃)COO^(n)C₅H₁₁ 2-271 F O 1 H CF₃ CH₃ H CH(CH₃)COO^(i)C₃H₇ 2-272 F O 1 H CF₃ CH₃ H CH(CH₃)COO^(c)C₅H₉ 2-273 F O 1 H CF₃ CH₃ H CH(CH₃)COO^(c)C₆H₁₁ 2-274 F O 1 H CF₃ CH₃ CH₃ H 2-275 F O 1 H CF₃ CH₃ CH₃ CH₃ 2-276 F O 1 H CF₃ CH₃ CH₃ C₂H₅ 2-277 F O 1 H CF₃ CH₃ CH₃ ^(n)C₃H₇ 2-278 F O 1 H CF₃ CH₃ CH₃ ^(i)C₃H₇ 2-279 F O 1 H CF₃ CH₃ CH₃ ^(i)C₄H₉ 2-280 F O 1 H CF₃ CH₃ CH₃ ^(n)C₄H₉ 2-281 F O 1 H CF₃ CH₃ CH₃ CH₂CH═CH₂ 2-282 F O 1 H CF₃ CH₃ CH₃ CH(CH₃)CH═CH₂ 2-283 F O 1 H CF₃ CH₃ CH₃ CH₂C≡CH 2-284 F O 1 H CF₃ CH₃ CH₃ CH(CH₃)C≡CH 2-285 F O 1 H CF₃ CH₃ CH₃ CH₂OCH₃ 2-286 F O 1 H CF₃ CH₃ CH₃ CH₂OC₂H₅ 2-287 H S 0 H CF₃ CH₃ — H 2-288 H S 0 H CF₃ CH₃ — CH₃ 2-289 H S 0 H CF₃ CH₃ — C₂H₅ 2-290 H S 0 H CF₃ CH₃ — ^(n)C₃H₇ 2-291 H S 0 H CF₃ CH₃ — ^(n)C₄H₉ 2-292 H S 0 H CF₃ CH₃ — ^(i)C₄H₉ 2-293 H S 0 H CF₃ CH₃ — ^(i)C₃H₇ 2-294 H S 0 H CF₃ CH₃ — CH₂CH₂Cl 2-295 H S 0 H CF₃ CH₃ — CH₂CH₂Br 2-296 H S 0 H CF₃ CH₃ — CH₂CH═CH₂ 2-297 H S 0 H CF₃ CH₃ — CH(CH₃)CH═CH₂ 2-298 H S 0 H CF₃ CH₃ — CH₂CCl═CH₂ 2-299 H S 0 H CF₃ CH₃ — CH₂C≡CH 2-300 H S 0 H CF₃ CH₃ — CH(CH₃)C≡CH 2-301 H S 0 H CF₃ CH₃ — CH₂CN 2-302 H S 0 H CF₃ CH₃ — CH₂OCH₃ 2-303 H S 0 H CF₃ CH₃ — CH₂OC₂H₅ 2-304 H S 0 H CF₃ CH₃ — CH₂COOH 2-305 H S 0 H CF₃ CH₃ — CH₂COOCH₃ 2-306 H S 0 H CF₃ CH₃ — CH₂COOC₂H₅ 2-307 H S 0 H CF₃ CH₃ — CH₂COO^(n)C₃H₇ 2-308 H S 0 H CF₃ CH₃ — CH₂COO^(n)C₄H₉ 2-309 H S 0 H CF₃ CH₃ — CH₂COO^(n)C₅H₁₁ 2-310 H S 0 H CF₃ CH₃ — CH₂COO^(i)C₃H₇ 2-311 H S 0 H CF₃ CH₃ — CH₂COO^(c)C₅H₉ 2-312 H S 0 H CF₃ CH₃ — CH₂COO^(c)C₆H₁₁ 2-313 H S 0 H CF₃ CH₃ — CH(CH₃)COOH 2-314 H S 0 H CF₃ CH₃ — CH(CH₃)COOCH₃ 2-315 H S 0 H CF₃ CH₃ — CH(CH₃)COOC₂H₅ 2-316 H S 0 H CF₃ CH₃ — CH(CH₃)COO^(n)C₃H₇ 2-317 H S 0 H CF₃ CH₃ — CH(CH₃)COO^(n)C₄H₉ 2-318 H S 0 H CF₃ CH₃ — CH(CH₃)COO^(n)C₅H₁₁ 2-319 H S 0 H CF₃ CH₃ — CH(CH₃)COO^(i)C₃H₇ 2-320 H S 0 H CF₃ CH₃ — CH(CH₃)COO^(c)C₅H₉ 2-321 H S 0 H CF₃ CH₃ — CH(CH₃)COO^(c)C₆H₁₁ 2-322 F S 0 H CF₃ CH₃ — H 2-323 F S 0 H CF₃ CH₃ — CH₃ 2-324 F S 0 H CF₃ CH₃ — C₂H₅ 2-325 F S 0 H CF₃ CH₃ — ^(n)C₃H₇ 2-326 F S 0 H CF₃ CH₃ — ^(n)C₄H₉ 2-327 F S 0 H CF₃ CH₃ — ^(i)C₃H₇ 2-328 F S 0 H CF₃ CH₃ — ^(s)C₄H₉ 2-329 F S 0 H CF₃ CH₃ — CH₂CH₂Cl 2-330 F S 0 H CF₃ CH₃ — CH₂CH₂Br 2-331 F S 0 H CF₃ CH₃ — CH₂CH═CH₂ 2-332 F S 0 H CF₃ CH₃ — CH(CH₃)CH═CH₂ 2-333 F S 0 H CF₃ CH₃ — CH₂CCl═CH₂ 2-334 F S 0 H CF₃ CH₃ — CH₂C≡CH 2-335 F S 0 H CF₃ CH₃ — CH(CH₃)C≡CH 2-336 F S 0 H CF₃ CH₃ — CH₂CN 2-337 F S 0 H CF₃ CH₃ — CH₂OCH₃ 2-338 F S 0 H CF₃ CH₃ — CH₂OC₂H₅ 2-339 F S 0 H CF₃ CH₃ — CH₂COOH 2-340 F S 0 H CF₃ CH₃ — CH₂COOCH₃ 2-341 F S 0 H CF₃ CH₃ — CH₂COOC₂H₅ 2-342 F S 0 H CF₃ CH₃ — CH₂COO^(n)C₃H₇ 2-343 F S 0 H CF₃ CH₃ — CH₂COO^(n)C₄H₉ 2-344 F S 0 H CF₃ CH₃ — CH₂COO^(n)C₅H₁₁ 2-345 F S 0 H CF₃ CH₃ — CH₂COO^(i)C₃H₇ 2-346 F S 0 H CF₃ CH₃ — CH₂COO^(c)C₅H₉ 2-347 F S 0 H CF₃ CH₃ — CH₂COO^(c)C₆H₁₁ 2-348 F S 0 H CF₃ CH₃ — CH(CH₃)COOH 2-349 F S 0 H CF₃ CH₃ — CH(CH₃)COOCH₃ 2-350 F S 0 H CF₃ CH₃ — CH(CH₃)COOC₂H₅ 2-351 F S 0 H CF₃ CH₃ — CH(CH₃)COO^(n)C₃H₇ 2-352 F S 0 H CF₃ CH₃ — CH(CH₃)COO^(n)C₄H₉ 2-353 F S 0 H CF₃ CH₃ — CH(CH₃)COO^(n)C₅H₁₁ 2-354 F S 0 H CF₃ CH₃ — CH(CH₃)COO^(i)C₃H₇ 2-355 F S 0 H CF₃ CH₃ — CH(CH₃)COO^(c)C₅H₉ 2-356 F S 0 H CF₃ CH₃ — CH(CH₃)COO^(c)C₆H₁₁ 2-357 H O 0 H CF₃ CH₃ — H 2-358 H O 0 H CF₃ CH₃ — CH₃ 2-359 H O 0 H CF₃ CH₃ — C₂H₅ 2-360 H O 0 H CF₃ CH₃ — ^(n)C₃H₇ 2-361 H O 0 H CF₃ CH₃ — ^(n)C₄H₉ 2-362 H O 0 H CF₃ CH₃ — ^(i)C₃H₇ 2-363 H O 0 H CF₃ CH₃ — ^(i)C₄H₉ 2-364 H O 0 H CF₃ CH₃ — CH₂CH═CH₂ 2-365 H O 0 H CF₃ CH₃ — CH(CH₃)CH═CH₂ 2-366 H O 0 H CF₃ CH₃ — CH₂C≡CH 2-367 H O 0 H CF₃ CH₃ — CH(CH₃)C≡CH 2-368 H O 0 H CF₃ CH₃ — CH₂OCH₃ 2-369 H O 0 H CF₃ CH₃ — CH₂OC₂H₅ 2-370 F O 0 H CF₃ CH₃ — H 2-371 F O 0 H CF₃ CH₃ — CH₃ 2-372 F O 0 H CF₃ CH₃ — C₂H₅ 2-373 F O 0 H CF₃ CH₃ — ^(n)C₃H₇ 2-374 F O 0 H CF₃ CH₃ — ^(n)C₄H₉ 2-375 F O 0 H CF₃ CH₃ — CH₂CH═CH₂ 2-376 F O 0 H CF₃ CH₃ — CH(CH₃)CH═CH₂ 2-377 F O 0 H CF₃ CH₃ — CH₂C≡CH 2-378 F O 0 H CF₃ CH₃ — CH(CH₃)C≡CH 2-379 F O 0 H CF₃ CH₃ — CH₂OCH₃ 2-380 F O 0 H CF₃ CH₃ — CH₂OC₂H₅ 2-381 H O 1 H CF₂Cl H H H 2-382 H O 1 H CF₂Cl H H CH₃ 2-383 H O 1 H CF₂Cl H H C₂H₅ 2-384 H O 1 H CF₂Cl H H ^(n)C₃H₇ 2-385 H O 1 H CF₂Cl H H ^(i)C₃H₇ 2-386 H O 1 H CF₂Cl H H ^(i)C₄H₉ 2-387 H O 1 H CF₂Cl H H ^(n)C₄H₉ 2-388 H O 1 H CF₂Cl H H CH₂CH₂Cl 2-389 H O 1 H CF₂Cl H H CH₂CH₂Br 2-390 H O 1 H CF₂Cl H H CH₂CH═CH₂ 2-391 H O 1 H CF₂Cl H H CH(CH₃)CH═CH₂ 2-392 H O 1 H CF₂Cl H H CH₂CCl═CH₂ 2-393 H O 1 H CF₂Cl H H CH₂C≡CH 2-394 H O 1 H CF₂Cl H H CH(CH₃)C≡CH 2-395 H O 1 H CF₂Cl H H CH₂CN 2-396 H O 1 H CF₂Cl H H CH₂OCH₃ 2-397 H O 1 H CF₂Cl H H CH₂OC₂H₅ 2-398 H O 1 H CF₂Cl H H CH₂COOH 2-399 H O 1 H CF₂Cl H H CH₂COOCH₃ 2-400 H O 1 H CF₂Cl H H CH₂COOC₂H₅ 2-401 H O 1 H CF₂Cl H H CH₂COO^(n)C₃H₇ 2-402 H O 1 H CF₂Cl H H CH₂COO^(n)C₄H₉ 2-403 H O 1 H CF₂Cl H H CH₂COO^(n)C₅H₁₁ 2-404 H O 1 H CF₂Cl H H CH₂COO^(i)C₃H₇ 2-405 H O 1 H CF₂Cl H H CH₂COO^(c)C₅H₉ 2-406 H O 1 H CF₂Cl H H CH₂COO^(c)C₆H₁₁ 2-407 H O 1 H CF₂Cl H H CH(CH₃)COOH 2-408 H O 1 H CF₂Cl H H CH(CH₃)COOCH₃ 2-409 H O 1 H CF₂Cl H H CH(CH₃)COOC₂H₅ 2-410 H O 1 H CF₂Cl H H CH(CH₃)COO^(n)C₃H₇ 2-411 H O 1 H CF₂Cl H H CH(CH₃)COO^(n)C₄H₉ 2-412 H O 1 H CF₂Cl H H CH(CH₃)COO^(n)C₅H₁₁ 2-413 H O 1 H CF₂Cl H H CH(CH₃)COO^(i)C₃H₇ 2-414 H O 1 H CF₂Cl H H CH(CH₃)COO^(c)C₅H₉ 2-415 H O 1 H CF₂Cl H H CH(CH₃)COO^(c)C₆H₁₁ 2-416 H O 1 H CF₂Cl H CH₃ H 2-417 H O 1 H CF₂Cl H CH₃ CH₃ 2-418 H O 1 H CF₂Cl H CH₃ C₂H₅ 2-419 H O 1 H CF₂Cl H CH₃ ^(n)C₃H₇ 2-420 H O 1 H CF₂Cl H CH₃ ^(i)C₃H₇ 2-421 H O 1 H CF₂Cl H CH₃ ^(i)C₄H₉ 2-422 H O 1 H CF₂Cl H CH₃ ^(n)C₄H₉ 2-423 H O 1 H CF₂Cl H CH₃ CH₂CH═CH₂ 2-424 H O 1 H CF₂Cl H CH₃ CH(CH₃)CH═CH₂ 2-425 H O 1 H CF₂Cl H CH₃ CH₂C≡CH 2-426 H O 1 H CF₂Cl H CH₃ CH(CH₃)C≡CH 2-427 H O 1 H CF₂Cl H CH₃ CH₂OCH₃ 2-428 H O 1 H CF₂Cl H CH₃ CH₂OC₂H₅ 2-429 F O 1 H CF₂Cl H H H 2-430 F O 1 H CF₂Cl H H CH₃ 2-431 F O 1 H CF₂Cl H H C₂H₅ 2-432 F O 1 H CF₂Cl H H ^(n)C₃H₇ 2-433 F O 1 H CF₂Cl H H ^(i)C₃H₇ 2-434 F O 1 H CF₂Cl H H ^(i)C₄H₉ 2-435 F O 1 H CF₂Cl H H ^(n)C₄H₉ 2-436 F O 1 H CF₂Cl H H CH₂CH₂Cl 2-437 F O 1 H CF₂Cl H H CH₂CH₂Br 2-438 F O 1 H CF₂Cl H H CH₂CH═CH₂ 2-439 F O 1 H CF₂Cl H H CH(CH₃)CH═CH₂ 2-440 F O 1 H CF₂Cl H H CH₂CCl═CH₂ 2-441 F O 1 H CF₂Cl H H CH₂C≡CH 2-442 F O 1 H CF₂Cl H H CH(CH₃)C≡CH 2-443 F O 1 H CF₂Cl H H CH₂CN 2-444 F O 1 H CF₂Cl H H CH₂OCH₃ 2-445 F O 1 H CF₂Cl H H CH₂OC₂H₅ 2-446 F O 1 H CF₂Cl H H CH₂COOH 2-447 F O 1 H CF₂Cl H H CH₂COOCH₃ 2-448 F O 1 H CF₂Cl H H CH₂COOC₂H₅ 2-449 F O 1 H CF₂Cl H H CH₂COO^(n)C₃H₇ 2-450 F O 1 H CF₂Cl H H CH₂COO^(n)C₄H₉ 2-451 F O 1 H CF₂Cl H H CH₂COO^(n)C₅H₁₁ 2-452 F O 1 H CF₂Cl H H CH₂COO^(i)C₃H₇ 2-453 F O 1 H CF₂Cl H H CH₂COO^(c)C₅H₉ 2-454 F O 1 H CF₂Cl H H CH₂COO^(c)C₆H₁₁ 2-455 F O 1 H CF₂Cl H H CH(CH₃)COOH 2-456 F O 1 H CF₂Cl H H CH(CH₃)COOCH₃ 2-457 F O 1 H CF₂Cl H H CH(CH₃)COOC₂H₅ 2-458 F O 1 H CF₂Cl H H CH(CH₃)COO^(n)C₃H₇ 2-459 F O 1 H CF₂Cl H H CH(CH₃)COO^(n)C₄H₉ 2-460 F O 1 H CF₂Cl H H CH(CH₃)COO^(n)C₅H₁₁ 2-461 F O 1 H CF₂Cl H H CH(CH₃)COO^(i)C₃H₇ 2-462 F O 1 H CF₂Cl H H CH(CH₃)COO^(c)C₅H₉ 2-463 F O 1 H CF₂Cl H H CH(CH₃)COO^(c)C₆H₁₁ 2-464 F O 1 H CF₂Cl H CH₃ H 2-465 F O 1 H CF₂Cl H CH₃ CH₃ 2-466 F O 1 H CF₂Cl H CH₃ C₂H₅ 2-467 F O 1 H CF₂Cl H CH₃ ^(n)C₃H₇ 2-468 F O 1 H CF₂Cl H CH₃ ^(i)C₃H₇ 2-469 F O 1 H CF₂Cl H CH₃ ^(i)C₄H₉ 2-470 F O 1 H CF₂Cl H CH₃ ^(n)C₄H₉ 2-471 F O 1 H CF₂Cl H CH₃ CH₂CH═CH₂ 2-472 F O 1 H CF₂Cl H CH₃ CH(CH₃)CH═CH₂ 2-473 F O 1 H CF₂Cl H CH₃ CH₂C≡CH 2-474 F O 1 H CF₂Cl H CH₃ CH(CH₃)C≡CH 2-475 F O 1 H CF₂Cl H CH₃ CH₂OCH₃ 2-476 F O 1 H CF₂Cl H CH₃ CH₂OC₂H₅ 2-477 H S 0 H CF₂Cl H — H 2-478 H S 0 H CF₂Cl H — CH₃ 2-479 H S 0 H CF₂Cl H — C₂H₅ 2-480 H S 0 H CF₂Cl H — ^(n)C₃H₇ 2-481 H S 0 H CF₂Cl H — ^(n)C₄H₉ 2-482 H S 0 H CF₂Cl H — ^(i)C₃H₇ 2-483 H S 0 H CF₂Cl H — ^(i)C₄H₉ 2-484 H S 0 H CF₂Cl H — CH₂CH₂Cl 2-485 H S 0 H CF₂Cl H — CH₂CH₂Br 2-486 H S 0 H CF₂Cl H — CH₂CH═CH₂ 2-487 H S 0 H CF₂Cl H — CH(CH₃)CH═CH₂ 2-488 H S 0 H CF₂Cl H — CH₂CCl═CH₂ 2-489 H S 0 H CF₂Cl H — CH₂C≡CH 2-490 H S 0 H CF₂Cl H — CH(CH₃)C≡CH 2-491 H S 0 H CF₂Cl H — CH₂CN 2-492 H S 0 H CF₂Cl H — CH₂OCH₃ 2-493 H S 0 H CF₂Cl H — CH₂OC₂H₅ 2-494 H S 0 H CF₂Cl H — CH₂COOH 2-495 H S 0 H CF₂Cl H — CH₂COOCH₃ 2-496 H S 0 H CF₂Cl H — CH₂COOC₂H₅ 2-497 H S 0 H CF₂Cl H — CH₂COO^(n)C₃H₇ 2-498 H S 0 H CF₂Cl H — CH₂COO^(n)C₄H₉ 2-499 H S 0 H CF₂Cl H — CH₂COO^(n)C₅H₁₁ 2-500 H S 0 H CF₂Cl H — CH₂COO^(i)C₃H₇ 2-501 H S 0 H CF₂Cl H — CH₂COO^(c)C₅H₉ 2-502 H S 0 H CF₂Cl H — CH₂COO^(c)C₆H₁₁ 2-503 H S 0 H CF₂Cl H — CH(CH₃)COOH 2-504 H S 0 H CF₂Cl H — CH(CH₃)COOCH₃ 2-505 H S 0 H CF₂Cl H — CH(CH₃)COOC₂H₅ 2-506 H S 0 H CF₂Cl H — CH(CH₃)COO^(n)C₃H₇ 2-507 H S 0 H CF₂Cl H — CH(CH₃)COO^(n)C₄H₉ 2-508 H S 0 H CF₂Cl H — CH(CH₃)COO^(n)C₅H₁₁ 2-509 H S 0 H CF₂Cl H — CH(CH₃)COO^(i)C₃H₇ 2-510 H S 0 H CF₂Cl H — CH(CH₃)COO^(c)C₅H₉ 2-511 H S 0 H CF₂Cl H — CH(CH₃)COO^(c)C₆H₁₁ 2-512 F S 0 H CF₂Cl H — H 2-513 F S 0 H CF₂Cl H — CH₃ 2-514 F S 0 H CF₂Cl H — C₂H₅ 2-515 F S 0 H CF₂Cl H — ^(n)C₃H₇ 2-516 F S 0 H CF₂Cl H — ^(n)C₄H₉ 2-517 F S 0 H CF₂Cl H — ^(i)C₃H₇ 2-518 F S 0 H CF₂Cl H — ^(i)C₄H₉ 2-519 F S 0 H CF₂Cl H — CH₂CH₂Cl 2-520 F S 0 H CF₂Cl H — CH₂CH₂Br 2-521 F S 0 H CF₂Cl H — CH₂CH═CH₂ 2-522 F S 0 H CF₂Cl H — CH(CH₃)CH═CH₂ 2-523 F S 0 H CF₂Cl H — CH₂CCl═CH₂ 2-524 F S 0 H CF₂Cl H — CH₂C≡CH 2-525 F S 0 H CF₂Cl H — CH(CH₃)C≡CH 2-526 F S 0 H CF₂Cl H — CH₂CN 2-527 F S 0 H CF₂Cl H — CH₂OCH₃ 2-528 F S 0 H CF₂Cl H — CH₂OC₂H₅ 2-529 F S 0 H CF₂Cl H — CH₂COOH 2-530 F S 0 H CF₂Cl H — CH₂COOCH₃ 2-531 F S 0 H CF₂Cl H — CH₂COOC₂H₅ 2-532 F S 0 H CF₂Cl H — CH₂COO^(n)C₃H₇ 2-533 F S 0 H CF₂Cl H — CH₂COO^(n)C₄H₉ 2-534 F S 0 H CF₂Cl H — CH₂COO^(n)C₅H₁₁ 2-535 F S 0 H CF₂Cl H — CH₂COO^(i)C₃H₇ 2-536 F S 0 H CF₂Cl H — CH₂COO^(c)C₅H₉ 2-537 F S 0 H CF₂Cl H — CH₂COO^(c)C₆H₁₁ 2-538 F S 0 H CF₂Cl H — CH(CH₃)COOH 2-539 F S 0 H CF₂Cl H — CH(CH₃)COOCH₃ 2-540 F S 0 H CF₂Cl H — CH(CH₃)COOC₂H₅ 2-541 F S 0 H CF₂Cl H — CH(CH₃)COO^(n)C₃H₇ 2-542 F S 0 H CF₂Cl H — CH(CH₃)COO^(n)C₄H₉ 2-543 F S 0 H CF₂Cl H — CH(CH₃)COO^(n)C₅H₁₁ 2-544 F S 0 H CF₂Cl H — CH(CH₃)COO^(i)C₃H₇ 2-545 F S 0 H CF₂Cl H — CH(CH₃)COO^(c)C₅H₉ 2-546 F S 0 H CF₂Cl H — CH(CH₃)COO^(c)C₆H₁₁ 2-547 H O 0 H CF₂Cl H — H 2-548 H O 0 H CF₂Cl H — CH₃ 2-549 H O 0 H CF₂Cl H — C₂H₅ 2-550 H O 0 H CF₂Cl H — ^(n)C₃H₇ 2-551 H O 0 H CF₂Cl H — ^(n)C₄H₉ 2-552 H O 0 H CF₂Cl H — ^(i)C₃H₇ 2-553 H O 0 H CF₂Cl H — ^(i)C₄H₉ 2-554 H O 0 H CF₂Cl H — CH₂CH═CH₂ 2-555 H O 0 H CF₂Cl H — CH(CH₃)CH═CH₂ 2-556 H O 0 H CF₂Cl H — CH₂C≡CH 2-557 H O 0 H CF₂Cl H — CH(CH₃)C≡CH 2-558 H O 0 H CF₂Cl H — CH₂OCH₃ 2-559 H O 0 H CF₂Cl H — CH₂OC₂H₅ 2-560 F O 0 H CF₂Cl H — H 2-561 F O 0 H CF₂Cl H — CH₃ 2-562 F O 0 H CF₂Cl H — C₂H₅ 2-563 F O 0 H CF₂Cl H — ^(n)C₃H₇ 2-564 F O 0 H CF₂Cl H — ^(n)C₄H₉ 2-565 F O 0 H CF₂Cl H — CH₂CH═CH₂ 2-566 F O 0 H CF₂Cl H — CH(CH₃)CH═CH₂ 2-567 F O 0 H CF₂Cl H — CH₂C≡CH 2-568 F O 0 H CF₂Cl H — CH(CH₃)C≡CH 2-569 F O 0 H CF₂Cl H — CH₂OCH₃ 2-570 F O 0 H CF₂Cl H — CH₂OC₂H₅ 2-571 H O 1 H CF₃ H H H 2-572 H O 1 H CF₃ H H CH₃ 2-573 H O 1 H CF₃ H H C₂H₅ 2-574 H O 1 H CF₃ H H ^(n)C₃H₇ 2-575 H O 1 H CF₃ H H ^(i)C₃H₇ 2-576 H O 1 H CF₃ H H ^(i)C₄H₉ 2-577 H O 1 H CF₃ H H ^(n)C₄H₉ 2-578 H O 1 H CF₃ H H CH₂CH₂Cl 2-579 H O 1 H CF₃ H H CH₂CH₂Br 2-580 H O 1 H CF₃ H H CH₂CH═CH₂ 2-581 H O 1 H CF₃ H H CH(CH₃)CH═CH₂ 2-582 H O 1 H CF₃ H H CH₂CCl═CH₂ 2-583 H O 1 H CF₃ H H CH₂C≡CH 2-584 H O 1 H CF₃ H H CH(CH₃)C≡CH 2-585 H O 1 H CF₃ H H CH₂CN 2-586 H O 1 H CF₃ H H CH₂OCH₃ 2-587 H O 1 H CF₃ H H CH₂OC₂H₅ 2-588 H O 1 H CF₃ H H CH₂COOH 2-589 H O 1 H CF₃ H H CH₂COOCH₃ 2-590 H O 1 H CF₃ H H CH₂COOC₂H₅ 2-591 H O 1 H CF₃ H H CH₂COO^(n)C₃H₇ 2-592 H O 1 H CF₃ H H CH₂COO^(n)C₄H₉ 2-593 H O 1 H CF₃ H H CH₂COO^(n)C₅H₁₁ 2-594 H O 1 H CF₃ H H CH₂COO^(i)C₃H₇ 2-595 H O 1 H CF₃ H H CH₂COO^(c)C₅H₉ 2-596 H O 1 H CF₃ H H CH₂COO^(c)C₆H₁₁ 2-597 H O 1 H CF₃ H H CH(CH₃)COOH 2-598 H O 1 H CF₃ H H CH(CH₃)COOCH₃ 2-599 H O 1 H CF₃ H H CH(CH₃)COOC₂H₅ 2-600 H O 1 H CF₃ H H CH(CH₃)COO^(n)C₃H₇ 2-601 H O 1 H CF₃ H H CH(CH₃)COO^(n)C₄H₉ 2-602 H O 1 H CF₃ H H CH(CH₃)COO^(n)C₅H₁₁ 2-603 H O 1 H CF₃ H H CH(CH₃)COO^(i)C₃H₇ 2-604 H O 1 H CF₃ H H CH(CH₃)COO^(c)C₅H₉ 2-605 H O 1 H CF₃ H H CH(CH₃)COO^(c)C₆H₁₁ 2-606 H O 1 H CF₃ H CH₃ H 2-607 H O 1 H CF₃ H CH₃ CH₃ 2-608 H O 1 H CF₃ H CH₃ C₂H₅ 2-609 H O 1 H CF₃ H CH₃ ^(n)C₃H₇ 2-610 H O 1 H CF₃ H CH₃ ^(i)C₃H₇ 2-611 H O 1 H CF₃ H CH₃ ^(i)C₄H₉ 2-612 H O 1 H CF₃ H CH₃ ^(n)C₄H₉ 2-613 H O 1 H CF₃ H CH₃ CH₂CH═CH₂ 2-614 H O 1 H CF₃ H CH₃ CH(CH₃)CH═CH₂ 2-615 H O 1 H CF₃ H CH₃ CH₂C≡CH 2-616 H O 1 H CF₃ H CH₃ CH(CH₃)C≡CH 2-617 H O 1 H CF₃ H CH₃ CH₂OCH₃ 2-618 H O 1 H CF₃ H CH₃ CH₂OC₂H₅ 2-619 F O 1 H CF₃ H H H 2-620 F O 1 H CF₃ H H CH₃ 2-621 F O 1 H CF₃ H H C₂H₅ 2-622 F O 1 H CF₃ H H ^(n)C₃H₇ 2-623 F O 1 H CF₃ H H ^(i)C₃H₇ 2-624 F O 1 H CF₃ H H ^(i)C₄H₉ 2-625 F O 1 H CF₃ H H ^(n)C₄H₉ 2-626 F O 1 H CF₃ H H CH₂CH₂Cl 2-627 F O 1 H CF₃ H H CH₂CH₂Br 2-628 F O 1 H CF₃ H H CH₂CH═CH₂ 2-629 F O 1 H CF₃ H H CH(CH₃)CH═CH₂ 2-630 F O 1 H CF₃ H H CH₂CCl═CH₂ 2-631 F O 1 H CF₃ H H CH₂C≡CH 2-632 F O 1 H CF₃ H H CH(CH₃)C≡CH 2-633 F O 1 H CF₃ H H CH₂CN 2-634 F O 1 H CF₃ H H CH₂OCH₃ 2-635 F O 1 H CF₃ H H CH₂OC₂H₅ 2-636 F O 1 H CF₃ H H CH₂COOH 2-637 F O 1 H CF₃ H H CH₂COOCH₃ 2-638 F O 1 H CF₃ H H CH₂COOC₂H₅ 2-639 F O 1 H CF₃ H H CH₂COO^(n)C₃H₇ 2-640 F O 1 H CF₃ H H CH₂COO^(n)C₄H₉ 2-641 F O 1 H CF₃ H H CH₂COO^(n)C₅H₁₁ 2-642 F O 1 H CF₃ H H CH₂COO^(i)C₃H₇ 2-643 F O 1 H CF₃ H H CH₂COO^(c)C₅H₉ 2-644 F O 1 H CF₃ H H CH₂COO^(c)C₆H₁₁ 2-645 F O 1 H CF₃ H H CH(CH₃)COOH 2-646 F O 1 H CF₃ H H CH(CH₃)COOCH₃ 2-647 F O 1 H CF₃ H H CH(CH₃)COOC₂H₅ 2-648 F O 1 H CF₃ H H CH(CH₃)COO^(n)C₃H₇ 2-648 F O 1 H CF₃ H H CH(CH₃)COO^(n)C₄H₉ 2-650 F O 1 H CF₃ H H CH(CH₃)COO^(n)C₅H₁₁ 2-651 F O 1 H CF₃ H H CH(CH₃)COO^(i)C₃H₇ 2-652 F O 1 H CF₃ H H CH(CH₃)COO^(c)C₅H₉ 2-653 F O 1 H CF₃ H H CH(CH₃)COO^(c)C₆H₁₁ 2-654 F O 1 H CF₃ H CH₃ H 2-655 F O 1 H CF₃ H CH₃ CH₃ 2-656 F O 1 H CF₃ H CH₃ C₂H₅ 2-657 F O 1 H CF₃ H CH₃ ^(n)C₃H₇ 2-658 F O 1 H CF₃ H CH₃ ^(i)C₃H₇ 2-659 F O 1 H CF₃ H CH₃ ^(i)C₄H₉ 2-660 F O 1 H CF₃ H CH₃ ^(n)C₄H₉ 2-661 F O 1 H CF₃ H CH₃ CH₂CH═CH₂ 2-662 F O 1 H CF₃ H CH₃ CH(CH₃)CH═CH₂ 2-663 F O 1 H CF₃ H CH₃ CH₂C≡CH 2-664 F O 1 H CF₃ H CH₃ CH(CH₃)C≡CH 2-665 F O 1 H CF₃ H CH₃ CH₂OCH₃ 2-666 F O 1 H CF₃ H CH₃ CH₂OC₂H₅ 2-667 H S 0 H CF₃ H — H 2-668 H S 0 H CF₃ H — CH₃ 2-669 H S 0 H CF₃ H — C₂H₅ 2-670 H S 0 H CF₃ H — ^(n)C₃H₇ 2-671 H S 0 H CF₃ H — ^(n)C₄H₉ 2-672 H S 0 H CF₃ H — ^(i)C₃H₇ 2-673 H S 0 H CF₃ H — ^(i)C₄H₉ 2-674 H S 0 H CF₃ H — CH₂CH₂Cl 2-675 H S 0 H CF₃ H — CH₂CH₂Br 2-676 H S 0 H CF₃ H — CH₂CH═CH₂ 2-677 H S 0 H CF₃ H — CH(CH₃)CH═CH₂ 2-678 H S 0 H CF₃ H — CH₂CCl═CH₂ 2-679 H S 0 H CF₃ H — CH₂C≡CH 2-680 H S 0 H CF₃ H — CH(CH₃)C≡CH 2-681 H S 0 H CF₃ H — CH₂CN 2-682 H S 0 H CF₃ H — CH₂OCH₃ 2-683 H S 0 H CF₃ H — CH₂OC₂H₅ 2-684 H S 0 H CF₃ H — CH₂COOH 2-685 H S 0 H CF₃ H — CH₂COOCH₃ 2-686 H S 0 H CF₃ H — CH₂COOC₂H₅ 2-687 H S 0 H CF₃ H — CH₂COO^(n)C₃H₇ 2-688 H S 0 H CF₃ H — CH₂COO^(n)C₄H₉ 2-689 H S 0 H CF₃ H — CH₂COO^(n)C₅H₁₁ 2-690 H S 0 H CF₃ H — CH₂COO^(i)C₃H₇ 2-691 H S 0 H CF₃ H — CH₂COO^(c)C₅H₉ 2-692 H S 0 H CF₃ H — CH₂COO^(c)C₆H₁₁ 2-693 H S 0 H CF₃ H — CH(CH₃)COOH 2-694 H S 0 H CF₃ H — CH(CH₃)COOCH₃ 2-695 H S 0 H CF₃ H — CH(CH₃)COOC₂H₅ 2-696 H S 0 H CF₃ H — CH(CH₃)COO^(n)C₃H₇ 2-697 H S 0 H CF₃ H — CH(CH₃)COO^(n)C₄H₉ 2-698 H S 0 H CF₃ H — CH(CH₃)COO^(n)C₅H₁₁ 2-699 H S 0 H CF₃ H — CH(CH₃)COO^(i)C₃H₇ 2-700 H S 0 H CF₃ H — CH(CH₃)COO^(c)C₅H₉ 2-701 H S 0 H CF₃ H — CH(CH₃)COO^(c)C₆H₁₁ 2-702 F S 0 H CF₃ H — H 2-703 F S 0 H CF₃ H — CH₃ 2-704 F S 0 H CF₃ H — C₂H₅ 2-705 F S 0 H CF₃ H — ^(n)C₃H₇ 2-706 F S 0 H CF₃ H — ^(i)C₄H₉ 2-707 F S 0 H CF₃ H — ^(i)C₃H₇ 2-708 F S 0 H CF₃ H — ^(s)C₄H₉ 2-709 F S 0 H CF₃ H — CH₂CH₂Cl 2-710 F S 0 H CF₃ H — CH₂CH₂Br 2-711 F S 0 H CF₃ H — CH₂CH═CH₂ 2-712 F S 0 H CF₃ H — CH(CH₃)CH═CH₂ 2-713 F S 0 H CF₃ H — CH₂CCl═CH₂ 2-714 F S 0 H CF₃ H — CH₂C≡CH 2-715 F S 0 H CF₃ H — CH(CH₃)C≡CH 2-716 F S 0 H CF₃ H — CH₂CN 2-717 F S 0 H CF₃ H — CH₂OCH₃ 2-718 F S 0 H CF₃ H — CH₂OC₂H₅ 2-719 F S 0 H CF₃ H — CH₂COOH 2-720 F S 0 H CF₃ H — CH₂COOCH₃ 2-721 F S 0 H CF₃ H — CH₂COOC₂H₅ 2-722 F S 0 H CF₃ H — CH₂COO^(n)C₃H₇ 2-723 F S 0 H CF₃ H — CH₂COO^(n)C₄H₉ 2-724 F S 0 H CF₃ H — CH₂COO^(n)C₅H₁₁ 2-725 F S 0 H CF₃ H — CH₂COO^(i)C₃H₇ 2-726 F S 0 H CF₃ H — CH₂COO^(c)C₅H₉ 2-727 F S 0 H CF₃ H — CH₂COO^(c)C₆H₁₁ 2-728 F S 0 H CF₃ H — CH(CH₃)COOH 2-729 F S 0 H CF₃ H — CH(CH₃)COOCH₃ 2-730 F S 0 H CF₃ H — CH(CH₃)COOC₂H₅ 2-731 F S 0 H CF₃ H — CH(CH₃)COO^(n)C₃H₇ 2-732 F S 0 H CF₃ H — CH(CH₃)COO^(n)C₄H₉ 2-733 F S 0 H CF₃ H — CH(CH₃)COO^(n)C₅H₁₁ 2-734 F S 0 H CF₃ H — CH(CH₃)COO^(i)C₃H₇ 2-735 F S 0 H CF₃ H — CH(CH₃)COO^(c)C₅H₉ 2-736 F S 0 H CF₃ H — CH(CH₃)COO^(c)C₆H₁₁ 2-737 H O 0 H CF₃ H — H 2-738 H O 0 H CF₃ H — CH₃ 2-739 H O 0 H CF₃ H — C₂H₅ 2-740 H O 0 H CF₃ H — ^(n)C₃H₇ 2-741 H O 0 H CF₃ H — ^(n)C₄H₉ 2-742 H O 0 H CF₃ H — ^(i)C₃H₇ 2-743 H O 0 H CF₃ H — ^(i)C₄H₉ 2-744 H O 0 H CF₃ H — CH₂CH═CH₂ 2-745 H O 0 H CF₃ H — CH(CH₃)CH═CH₂ 2-746 H O 0 H CF₃ H — CH₂C≡CH 2-747 H O 0 H CF₃ H — CH(CH₃)C≡CH 2-748 H O 0 H CF₃ H — CH₂OCH₃ 2-749 H O 0 H CF₃ H — CH₂OC₂H₅ 2-750 F O 0 H CF₃ H — H 2-751 F O 0 H CF₃ H — CH₃ 2-752 F O 0 H CF₃ H — C₂H₅ 2-753 F O 0 H CF₃ H — ^(n)C₃H₇ 2-754 F O 0 H CF₃ H — ^(n)C₄H₉ 2-755 F O 0 H CF₃ H — CH₂CH═CH₂ 2-756 F O 0 H CF₃ H — CH(CH₃)CH═CH₂ 2-757 F O 0 H CF₃ H — CH₂C≡CH 2-758 F O 0 H CF₃ H — CH(CH₃)C≡CH 2-759 F O 0 H CF₃ H — CH₂OCH₃ 2-760 F O 0 H CF₃ H — CH₂OC₂H₅ 2-761 H O 1 CH₃ CF₃ H H H 2-762 H O 1 CH₃ CF₃ H H CH₃ 2-763 H O 1 CH₃ CF₃ H H C₂H₅ 2-764 H O 1 CH₃ CF₃ H H ^(n)C₃H₇ 2-765 H O 1 CH₃ CF₃ H H ^(i)C₃H₇ 2-766 H O 1 CH₃ CF₃ H H ^(i)C₄H₉ 2-767 H O 1 CH₃ CF₃ H H ^(n)C₄H₉ 2-768 H O 1 CH₃ CF₃ H H CH₂CH₂Cl 2-769 H O 1 CH₃ CF₃ H H CH₂CH₂Br 2-770 H O 1 CH₃ CF₃ H H CH₂CH═CH₂ 2-771 H O 1 CH₃ CF₃ H H CH(CH₃)CH═CH₂ 2-772 H O 1 CH₃ CF₃ H H CH₂CCl═CH₂ 2-773 H O 1 CH₃ CF₃ H H CH₂C≡CH 2-774 H O 1 CH₃ CF₃ H H CH(CH₃)C≡CH 2-775 H O 1 CH₃ CF₃ H H CH₂CN 2-776 H O 1 CH₃ CF₃ H H CH₂OCH₃ 2-777 H O 1 CH₃ CF₃ H H CH₂OC₂H₅ 2-778 H O 1 CH₃ CF₃ H H CH₂COOH 2-779 H O 1 CH₃ CF₃ H H CH₂COOCH₃ 2-780 H O 1 CH₃ CF₃ H H CH₂COOC₂H₅ 2-781 H O 1 CH₃ CF₃ H H CH₂COO^(n)C₃H₇ 2-782 H O 1 CH₃ CF₃ H H CH₂COO^(n)C₄H₉ 2-783 H O 1 CH₃ CF₃ H H CH₂COO^(n)C₅H₁₁ 2-784 H O 1 CH₃ CF₃ H H CH₂COO^(i)C₃H₇ 2-785 H O 1 CH₃ CF₃ H H CH₂COO^(c)C₅H₉ 2-786 H O 1 CH₃ CF₃ H H CH₂COO^(c)C₆H₁₁ 2-787 H O 1 CH₃ CF₃ H H CH(CH₃)COOH 2-788 H O 1 CH₃ CF₃ H H CH(CH₃)COOCH₃ 2-789 H O 1 CH₃ CF₃ H H CH(CH₃)COOC₂H₅ 2-790 H O 1 CH₃ CF₃ H H CH(CH₃)COO^(n)C₃H₇ 2-791 H O 1 CH₃ CF₃ H H CH(CH₃)COO^(n)C₄H₉ 2-792 H O 1 CH₃ CF₃ H H CH(CH₃)COO^(n)C₅H₁₁ 2-793 H O 1 CH₃ CF₃ H H CH(CH₃)COO^(i)C₃H₇ 2-794 H O 1 CH₃ CF₃ H H CH(CH₃)COO^(c)C₅H₉ 2-795 H O 1 CH₃ CF₃ H H CH(CH₃)COO^(c)C₆H₁₁ 2-796 H O 1 CH₃ CF₃ H CH₃ H 2-797 H O 1 CH₃ CF₃ H CH₃ CH₃ 2-798 H O 1 CH₃ CF₃ H CH₃ C₂H₅ 2-799 H O 1 CH₃ CF₃ H CH₃ ^(n)C₃H₇ 2-800 H O 1 CH₃ CF₃ H CH₃ ^(i)C₃H₇ 2-801 H O 1 CH₃ CF₃ H CH₃ ^(i)C₄H₉ 2-802 H O 1 CH₃ CF₃ H CH₃ ^(n)C₄H₉ 2-803 H O 1 CH₃ CF₃ H CH₃ CH₂CH═CH₂ 2-804 H O 1 CH₃ CF₃ H CH₃ CH(CH₃)CH═CH₂ 2-805 H O 1 CH₃ CF₃ H CH₃ CH₂C≡CH 2-806 H O 1 CH₃ CF₃ H CH₃ CH(CH₃)C≡CH 2-807 H O 1 CH₃ CF₃ H CH₃ CH₂OCH₃ 2-808 H O 1 CH₃ CF₃ H CH₃ CH₂OC₂H₅ 2-809 F O 1 CH₃ CF₃ H H H 2-810 F O 1 CH₃ CF₃ H H CH₃ 2-811 F O 1 CH₃ CF₃ H H C₂H₅ 2-812 F O 1 CH₃ CF₃ H H ^(n)C₃H₇ 2-813 F O 1 CH₃ CF₃ H H ^(i)C₃H₇ 2-814 F O 1 CH₃ CF₃ H H ^(i)C₄H₉ 2-815 F O 1 CH₃ CF₃ H H ^(n)C₄H₉ 2-816 F O 1 CH₃ CF₃ H H CH₂CH₂Cl 2-817 F O 1 CH₃ CF₃ H H CH₂CH₂Br 2-818 F O 1 CH₃ CF₃ H H CH₂CH═CH₂ 2-819 F O 1 CH₃ CF₃ H H CH(CH₃)CH═CH₂ 2-820 F O 1 CH₃ CF₃ H H CH₂CCl═CH₂ 2-821 F O 1 CH₃ CF₃ H H CH₂C≡CH 2-822 F O 1 CH₃ CF₃ H H CH(CH₃)C≡CH 2-823 F O 1 CH₃ CF₃ H H CH₂CN 2-824 F O 1 CH₃ CF₃ H H CH₂OCH₃ 2-825 F O 1 CH₃ CF₃ H H CH₂OC₂H₅ 2-826 F O 1 CH₃ CF₃ H H CH₂COOH 2-827 F O 1 CH₃ CF₃ H H CH₂COOCH₃ 2-828 F O 1 CH₃ CF₃ H H CH₂COOC₂H₅ 2-829 F O 1 CH₃ CF₃ H H CH₂COO^(n)C₃H₇ 2-830 F O 1 CH₃ CF₃ H H CH₂COO^(n)C₄H₉ 2-831 F O 1 CH₃ CF₃ H H CH₂COO^(n)C₅H₁₁ 2-832 F O 1 CH₃ CF₃ H H CH₂COO^(i)C₃H₇ 2-833 F O 1 CH₃ CF₃ H H CH₂COO^(c)C₅H₉ 2-834 F O 1 CH₃ CF₃ H H CH₂COO^(c)C₆H₁₁ 2-835 F O 1 CH₃ CF₃ H H CH(CH₃)COOH 2-836 F O 1 CH₃ CF₃ H H CH(CH₃)COOCH₃ 2-837 F O 1 CH₃ CF₃ H H CH(CH₃)COOC₂H₅ 2-838 F O 1 CH₃ CF₃ H H CH(CH₃)COO^(n)C₃H₇ 2-839 F O 1 CH₃ CF₃ H H CH(CH₃)COO^(n)C₄H₉ 2-840 F O 1 CH₃ CF₃ H H CH(CH₃)COO^(n)C₅H₁₁ 2-841 F O 1 CH₃ CF₃ H H CH(CH₃)COO^(i)C₃H₇ 2-842 F O 1 CH₃ CF₃ H H CH(CH₃)COO^(c)C₅H₉ 2-843 F O 1 CH₃ CF₃ H H CH(CH₃)COO^(c)C₆H₁₁ 2-843 F O 1 CH₃ CF₃ H CH₃ H 2-845 F O 1 CH₃ CF₃ H CH₃ CH₃ 2-846 F O 1 CH₃ CF₃ H CH₃ C₂H₅ 2-847 F O 1 CH₃ CF₃ H CH₃ ^(n)C₃H₇ 2-848 F O 1 CH₃ CF₃ H CH₃ ^(i)C₃H₇ 2-849 F O 1 CH₃ CF₃ H CH₃ ^(i)C₄H₉ 2-850 F O 1 CH₃ CF₃ H CH₃ ^(n)C₄H₉ 2-851 F O 1 CH₃ CF₃ H CH₃ CH₂CH═CH₂ 2-852 F O 1 CH₃ CF₃ H CH₃ CH(CH₃)CH═CH₂ 2-853 F O 1 CH₃ CF₃ H CH₃ CH₂C≡CH 2-854 F O 1 CH₃ CF₃ H CH₃ CH(CH₃)C≡CH 2-855 F O 1 CH₃ CF₃ H CH₃ CH₂OCH₃ 2-856 F O 1 CH₃ CF₃ H CH₃ CH₂OC₂H₅ 2-857 H S 0 CH₃ CF₃ H — H 2-858 H S 0 CH₃ CF₃ H — CH₃ 2-859 H S 0 CH₃ CF₃ H — C₂H₅ 2-860 H S 0 CH₃ CF₃ H — ^(n)C₃H₇ 2-861 H S 0 CH₃ CF₃ H — ^(n)C₄H₉ 2-862 H S 0 CH₃ CF₃ H — ^(i)C₄H₉ 2-863 H S 0 CH₃ CF₃ H — ^(i)C₃H₇ 2-864 H S 0 CH₃ CF₃ H — CH₂CH₂Cl 2-865 H S 0 CH₃ CF₃ H — CH₂CH₂Br 2-866 H S 0 CH₃ CF₃ H — CH₂CH═CH₂ 2-867 H S 0 CH₃ CF₃ H — CH(CH₃)CH═CH₂ 2-868 H S 0 CH₃ CF₃ H — CH₂CCl═CH₂ 2-869 H S 0 CH₃ CF₃ H — CH₂C≡CH 2-870 H S 0 CH₃ CF₃ H — CH(CH₃)C≡CH 2-871 H S 0 CH₃ CF₃ H — CH₂CN 2-872 H S 0 CH₃ CF₃ H — CH₂OCH₃ 2-873 H S 0 CH₃ CF₃ H — CH₂OC₂H₅ 2-874 H S 0 CH₃ CF₃ H — CH₂COOH 2-875 H S 0 CH₃ CF₃ H — CH₂COOCH₃ 2-876 H S 0 CH₃ CF₃ H — CH₂COOC₂H₅ 2-877 H S 0 CH₃ CF₃ H — CH₂COO^(n)C₃H₇ 2-878 H S 0 CH₃ CF₃ H — CH₂COO^(n)C₄H₉ 2-879 H S 0 CH₃ CF₃ H — CH₂COO^(n)C₅H₁₁ 2-880 H S 0 CH₃ CF₃ H — CH₂COO^(i)C₃H₇ 2-881 H S 0 CH₃ CF₃ H — CH₂COO^(c)C₅H₉ 2-882 H S 0 CH₃ CF₃ H — CH₂COO^(c)C₆H₁₁ 2-883 H S 0 CH₃ CF₃ H — CH(CH₃)COOH 2-884 H S 0 CH₃ CF₃ H — CH(CH₃)COOCH₃ 2-885 H S 0 CH₃ CF₃ H — CH(CH₃)COOC₂H₅ 2-886 H S 0 CH₃ CF₃ H — CH(CH₃)COO^(n)C₃H₇ 2-887 H S 0 CH₃ CF₃ H — CH(CH₃)COO^(n)C₄H₉ 2-888 H S 0 CH₃ CF₃ H — CH(CH₃)COO^(n)C₅H₁₁ 2-889 H S 0 CH₃ CF₃ H — CH(CH₃)COO^(i)C₃H₇ 2-890 H S 0 CH₃ CF₃ H — CH(CH₃)COO^(c)C₅H₉ 2-891 H S 0 CH₃ CF₃ H — CH(CH₃)COO^(c)C₆H₁₁ 2-892 F S 0 CH₃ CF₃ H — H 2-893 F S 0 CH₃ CF₃ H — CH₃ 2-894 F S O CH₃ CF₃ H — C₂H₅ 2-895 F S O CH₃ CF₃ H — ^(n)C₃H₇ 2-896 F S 0 CH₃ CF₃ H — ^(n)C₄H₉ 2-897 F S 0 CH₃ CF₃ H — ^(i)C₃H₇ 2-898 F S 0 CH₃ CF₃ H — ^(s)C₄H₉ 2-899 F S 0 CH₃ CF₃ H — CH₂CH₂Cl 2-900 F S 0 CH₃ CF₃ H — CH₂CH₂Br 2-901 F S 0 CH₃ CF₃ H — CH₂CH═CH₂ 2-902 F S 0 CH₃ CF₃ H — CH(CH₃)CH═CH₂ 2-903 F S 0 CH₃ CF₃ H — CH₂CCl═CH₂ 2-904 F S 0 CH₃ CF₃ H — CH₂C≡CH 2-905 F S 0 CH₃ CF₃ H — CH(CH₃)C≡CH 2-906 F S 0 CH₃ CF₃ H — CH₂CN 2-907 F S 0 CH₃ CF₃ H — CH₂OCH₃ 2-908 F S 0 CH₃ CF₃ H — CH₂OC₂H₅ 2-909 F S 0 CH₃ CF₃ H — CH₂COOH 2-910 F S 0 CH₃ CF₃ H — CH₂COOCH₃ 2-911 F S 0 CH₃ CF₃ H — CH₂COOC₂H₅ 2-912 F S 0 CH₃ CF₃ H — CH₂COO^(n)C₃H₇ 2-913 F S 0 CH₃ CF₃ H — CH₂COO^(n)C₄H₉ 2-914 F S 0 CH₃ CF₃ H — CH₂COO^(n)C₅H₁₁ 2-915 F S 0 CH₃ CF₃ H — CH₂COO^(i)C₃H₇ 2-916 F S 0 CH₃ CF₃ H — CH₂COO^(c)C₅H₉ 2-917 F S 0 CH₃ CF₃ H — CH₂COO^(c)C₆H₁₁ 2-918 F S 0 CH₃ CF₃ H — CH(CH₃)COOH 2-919 F S 0 CH₃ CF₃ H — CH(CH₃)COOCH₃ 2-920 F S 0 CH₃ CF₃ H — CH(CH₃)COOC₂H₅ 2-921 F S 0 CH₃ CF₃ H — CH(CH₃)COO^(n)C₃H₇ 2-922 F S 0 CH₃ CF₃ H — CH(CH₃)COO^(n)C₄H₉ 2-923 F S 0 CH₃ CF₃ H — CH(CH₃)COO^(n)C₅H₁₁ 2-924 F S 0 CH₃ CF₃ H — CH(CH₃)COO^(i)C₃H₇ 2-925 F S 0 CH₃ CF₃ H — CH(CH₃)COO^(c)C₅H₉ 2-926 F S 0 CH₃ CF₃ H — CH(CH₃)COO^(c)C₆H₁₁ 2-927 H O 0 CH₃ CF₃ H — H 2-928 H O 0 CH₃ CF₃ H — CH₃ 2-929 H O 0 CH₃ CF₃ H — C₂H₅ 2-930 H O 0 CH₃ CF₃ H — ^(n)C₃H₇ 2-931 H O 0 CH₃ CF₃ H — ^(n)C₄H₉ 2-932 H O 0 CH₃ CF₃ H — ^(i)C₃H₇ 2-933 H O 0 CH₃ CF₃ H — ^(i)C₄H₉ 2-934 H O 0 CH₃ CF₃ H — CH₂CH═CH₂ 2-935 H O 0 CH₃ CF₃ H — CH(CH₃)CH═CH₂ 2-936 H O 0 CH₃ CF₃ H — CH₂C≡CH 2-937 H O 0 CH₃ CF₃ H — CH(CH₃)C≡CH 2-938 H O 0 CH₃ CF₃ H — CH₂OCH₃ 2-939 H O 0 CH₃ CF₃ H — CH₂OC₂H₅ 2-940 F O 0 CH₃ CF₃ H — H 2-941 F O 0 CH₃ CF₃ H — CH₃ 2-942 F O 0 CH₃ CF₃ H — C₂H₅ 2-943 F O 0 CH₃ CF₃ H — ^(n)C₃H₇ 2-944 F O 0 CH₃ CF₃ H — ^(n)C₄H₉ 2-945 F O 0 CH₃ CF₃ H — CH₂CH═CH₂ 2-946 F O 0 CH₃ CF₃ H — CH(CH₃)CH═CH₂ 2-947 F O 0 CH₃ CF₃ H — CH₂C≡CH 2-948 F O 0 CH₃ CF₃ H — CH(CH₃)C≡CH 2-949 F O 0 CH₃ CF₃ H — CH₂OCH₃ 2-950 F O 0 CH₃ CF₃ H — CH₂OC₂H₅

TABLE 3 Compounds of the formula:

Compound No. X Y Z² R³ R¹ R² R⁶ 3-1  H F O H CF₂Cl H CH₃ 3-2  H Cl O H CF₂Cl H CH₃ 3-3  H Br O H CF₂Cl H CH₃ 3-4  F F O H CF₂Cl H CH₃ 3-5  F Cl O H CF₂Cl H CH₃ 3-6  F Br O H CF₂Cl H CH₃ 3-7  H F O H CF₂Cl CH₃ CH₃ 3-8  H Cl O H CF₂Cl CH₃ CH₃ 3-9  H Br O H CF₂Cl CH₃ CH₃ 3-10  F F O H CF₂Cl CH₃ CH₃ 3-11  F Cl O H CF₂Cl CH₃ CH₃ 3-12  F Br O H CF₂Cl CH₃ CH₃ 3-13  H F O H CF₂Cl H C₂H₅ 3-14  H Cl O H CF₂Cl H C₂H₅ 3-15  H Br O H CF₂Cl H C₂H₅ 3-16  F F O H CF₂Cl H C₂H₅ 3-17  F Cl O H CF₂Cl H C₂H₅ 3-18  F Br O H CF₂Cl H C₂H₅ 3-19  H F O H CF₂Cl CH₃ C₂H₅ 3-20  H Cl O H CF₂Cl CH₃ C₂H₅ 3-21  H Br O H CF₂Cl CH₃ C₂H₅ 3-22  F F O H CF₂Cl CH₃ C₂H₅ 3-23  F Cl O H CF₂Cl CH₃ C₂H₅ 3-24  F Br O H CF₂Cl CH₃ C₂H₅ 3-25  H F O H CF₂Cl CH₃ CH₂Br 3-26  H F O H CF₂Cl CH₃ CHBr₂ 3-27  H F O H CF₂Cl CH₃ CBr₃ 3-28  H F O H CF₂Cl CH₃ CHO 3-29  H F O H CF₂Cl CH₃ CN 3-30  H F O H CF₂Cl CH₃ COOH 3-31  H F O H CF₂Cl CH₃ CH₂OH 3-32  H F O H CF₂Cl CH₃ CH₂OCH₃ 3-33  H F O H CF₂Cl CH₃ CH₂OC₂H₅ 3-34  H F O H CF₂Cl CH₃ CH₂O^(i)C₃H₇ 3-35  H F O H CF₂Cl CH₃ CH₂OCH₂OCH₃ 3-36  H F O H CF₂Cl CH₃ CH₂OCH₂OC₂H₅ 3-37  H F O H CF₂Cl CH₃ CH₂OCOCH₃ 3-38  H F O H CF₂Cl CH₃ CH₂OCOC₂H₅ 3-39  H F O H CF₂Cl CH₃ CH₂OCO^(i)C₃H₇ 3-40  H F O H CF₂Cl CH₃ CH₂OCOCH₂Cl 3-41  H F O H CF₂Cl CH₃ CH₂OCOCCl₃ 3-42  H F O H CF₂Cl CH₃ CH₂OCOCF₃ 3-43  H F O H CF₂Cl CH₃ COOCH₃ 3-44  H F O H CF₂Cl CH₃ COOC₂H₅ 3-45  H F O H CF₂Cl CH₃ COO^(n)C₃H₇ 3-46  H F O H CF₂Cl CH₃ COO^(n)C₄H₉ 3-47  H F O H CF₂Cl CH₃ COO^(n)C₅H₁₁ 3-48  H F O H CF₂Cl CH₃ COO^(i)C₃H₇ 3-49  H F O H CF₂Cl CH₃ COCH₃ 3-50  H F O H CF₂Cl CH₃ COC₂H₅ 3-51  H Cl O H CF₂Cl CH₃ CH₂Br 3-52  H Cl O H CF₂Cl CH₃ CHBr₂ 3-53  H Cl O H CF₂Cl CH₃ CBr₃ 3-54  H Cl O H CF₂Cl CH₃ CHO 3-55  H Cl O H CF₂Cl CH₃ CN 3-56  H Cl O H CF₂Cl CH₃ COOH 3-57  H Cl O H CF₂Cl CH₃ CH₂OH 3-58  H Cl O H CF₂Cl CH₃ CH₂OCH₃ 3-59  H Cl O H CF₂Cl CH₃ CH₂OC₂H₅ 3-60  H Cl O H CF₂Cl CH₃ CH₂O^(i)C₃H₇ 3-61  H Cl O H CF₂Cl CH₃ CH₂OCH₂OCH₃ 3-62  H Cl O H CF₂Cl CH₃ CH₂OCH₂OC₂H₅ 3-63  H Cl O H CF₂Cl CH₃ CH₂OCOCH₃ 3-64  H Cl O H CF₂Cl CH₃ CH₂OCOC₂H₅ 3-65  H Cl O H CF₂Cl CH₃ CH₂OCO^(i)C₃H₇ 3-66  H Cl O H CF₂Cl CH₃ CH₂OCOCH₂Cl 3-67  H Cl O H CF₂Cl CH₃ CH₂OCOCCl₃ 3-67  H Cl O H CF₂Cl CH₃ CH₂OCOCF₃ 3-69  H Cl O H CF₂Cl CH₃ COOCH₃ 3-70  H Cl O H CF₂Cl CH₃ COOC₂H₅ 3-71  H Cl O H CF₂Cl CH₃ COO^(n)C₃H₇ 3-72  H Cl O H CF₂Cl CH₃ COO^(n)C₄H₉ 3-73  H Cl O H CF₂Cl CH₃ COO^(n)C₅H₁₁ 3-74  H Cl O H CF₂Cl CH₃ COO^(i)C₃H₇ 3-75  H Cl O H CF₂Cl CH₃ COCH₃ 3-76  H Cl O H CF₂Cl CH₃ COC₂H₅ 3-77  F F O H CF₂Cl CH₃ CH₂Br 3-78  F F O H CF₂Cl CH₃ CHBr₂ 3-79  F F O H CF₂Cl CH₃ CBr₃ 3-80  F F O H CF₂Cl CH₃ CHO 3-81  F F O H CF₂Cl CH₃ CN 3-82  F F O H CF₂Cl CH₃ COOH 3-83  F F O H CF₂Cl CH₃ CH₂OH 3-84  F F O H CF₂Cl CH₃ CH₂OCH₃ 3-85  F F O H CF₂Cl CH₃ CH₂OC₂H₅ 3-86  F F O H CF₂Cl CH₃ CH₂O^(i)C₃H₇ 3-87  F F O H CF₂Cl CH₃ CH₂OCH₂OCH₃ 3-88  F F O H CF₂Cl CH₃ CH₂OCH₂OC₂H₅ 3-89  F F O H CF₂Cl CH₃ CH₂OCOCH₃ 3-90  F F O H CF₂Cl CH₃ CH₂OCOC₂H₅ 3-91  F F O H CF₂Cl CH₃ CH₂OCO^(i)C₃H₇ 3-92  F F O H CF₂Cl CH₃ CH₂OCOCH₂Cl 3-93  F F O H CF₂Cl CH₃ CH₂OCOCCl₃ 3-94  F F O H CF₂Cl CH₃ CH₂OCOCF₃ 3-95  F F O H CF₂Cl CH₃ COOCH₃ 3-96  F F O H CF₂Cl CH₃ COOC₂H₅ 3-97  F F O H CF₂Cl CH₃ COO^(n)C₃H₇ 3-98  F F O H CF₂Cl CH₃ COO^(n)C₄H₉ 3-99  F F O H CF₂Cl CH₃ COO^(n)C₅H₁₁ 3-100 F F O H CF₂Cl CH₃ COO^(i)C₃H₇ 3-101 F F O H CF₂Cl CH₃ COCH₃ 3-102 F F O H CF₂Cl CH₃ COC₂H₅ 3-103 F Cl O H CF₂Cl CH₃ CH₂Br 3-104 F Cl O H CF₂Cl CH₃ CHBr₂ 3-105 F Cl O H CF₂Cl CH₃ CBr₃ 3-106 F Cl O H CF₂Cl CH₃ CHO 3-107 F Cl O H CF₂Cl CH₃ CN 3-108 F Cl O H CF₂Cl CH₃ COOH 3-109 F Cl O H CF₂Cl CH₃ CH₂OH 3-110 F Cl O H CF₂Cl CH₃ CH₂OCH₃ 3-111 F Cl O H CF₂Cl CH₃ CH₂OC₂H₅ 3-112 F Cl O H CF₂Cl CH₃ CH₂O^(i)C₃H₇ 3-113 F Cl O H CF₂Cl CH₃ CH₂OCH₂OCH₃ 3-114 F Cl O H CF₂Cl CH₃ CH₂OCH₂OC₂H₅ 3-115 F Cl O H CF₂Cl CH₃ CH₂OCOCH₃ 3-116 F Cl O H CF₂Cl CH₃ CH₂OCOC₂H₅ 3-117 F Cl O H CF₂Cl CH₃ CH₂OCO^(i)C₃H₇ 3-118 F Cl O H CF₂Cl CH₃ CH₂OCOCH₂Cl 3-119 F Cl O H CF₂Cl CH₃ CH₂OCOCCl₃ 3-120 F Cl O H CF₂Cl CH₃ CH₂OCOCF₃ 3-121 F Cl O H CF₂Cl CH₃ COOCH₃ 3-122 F Cl O H CF₂Cl CH₃ COOC₂H₅ 3-123 F Cl O H CF₂Cl CH₃ COO^(n)C₃H₇ 3-124 F Cl O H CF₂Cl CH₃ COO^(n)C₄H₉ 3-125 F Cl O H CF₂Cl CH₃ COO^(n)C₅H₁₁ 3-126 F Cl O H CF₂Cl CH₃ COO^(i)C₃H₇ 3-127 F Cl O H CF₂Cl CH₃ COCH₃ 3-128 F Cl O H CF₂Cl CH₃ COC₂H₅ 3-129 H F O H CF₃ H CH₃ 3-130 H Cl O H CF₃ H CH₃ 3-131 H Br O H CF₃ H CH₃ 3-132 F F O H CF₃ H CH₃ 3-133 F Cl O H CF₃ H CH₃ 3-134 F Br O H CF₃ H CH₃ 3-135 H F O H CF₃ CH₃ CH₃ 3-136 H Cl O H CF₃ CH₃ CH₃ 3-137 H Br O H CF₃ CH₃ CH₃ 3-138 F F O H CF₃ CH₃ CH₃ 3-139 F Cl O H CF₃ CH₃ CH₃ 3-140 F Br O H CF₃ CH₃ CH₃ 3-141 H F O H CF₃ H C₂H₅ 3-142 H Cl O H CF₃ H C₂H₅ 3-143 H Br O H CF₃ H C₂H₅ 3-144 F F O H CF₃ H C₂H₅ 3-145 F Cl O H CF₃ H C₂H₅ 3-146 F Br O H CF₃ H C₂H₅ 3-147 H F O H CF₃ CH₃ C₂H₅ 3-148 H Cl O H CF₃ CH₃ C₂H₅ 3-149 H Br O H CF₃ CH₃ C₂H₅ 3-150 F F O H CF₃ CH₃ C₂H₅ 3-151 F Cl O H CF₃ CH₃ C₂H₅ 3-152 F Br O H CF₃ CH₃ C₂H₅ 3-153 H F O H CF₃ CH₃ CH₂Br 3-154 H F O H CF₃ CH₃ CHBr₂ 3-155 H F O H CF₃ CH₃ CBr₃ 3-156 H F O H CF₃ CH₃ CHO 3-157 H F O H CF₃ CH₃ CN 3-158 H F O H CF₃ CH₃ COOH 3-159 H F O H CF₃ CH₃ CH₂OH 3-160 H F O H CF₃ CH₃ CH₂OCH₃ 3-161 H F O H CF₃ CH₃ CH₂OC₂H₅ 3-162 H F O H CF₃ CH₃ CH₂O^(i)C₃H₇ 3-163 H F O H CF₃ CH₃ CH₂OCH₂OCH₃ 3-164 H F O H CF₃ CH₃ CH₂OCH₂OC₂H₅ 3-165 H F O H CF₃ CH₃ CH₂OCOCH₃ 3-166 H F O H CF₃ CH₃ CH₂OCOC₂H₅ 3-167 H F O H CF₃ CH₃ CH₂OCO^(i)C₃H₇ 3-168 H F O H CF₃ CH₃ CH₂OCOCH₂Cl 3-169 H F O H CF₃ CH₃ CH₂OCOCCl₃ 3-170 H F O H CF₃ CH₃ CH₂OCOCF₃ 3-171 H F O H CF₃ CH₃ COOCH₃ 3-172 H F O H CF₃ CH₃ COOC₂H₅ 3-173 H F O H CF₃ CH₃ COO^(n)C₃H₇ 3-174 H F O H CF₃ CH₃ COO^(n)C₄H₉ 3-175 H F O H CF₃ CH₃ COO^(n)C₅H₁₁ 3-176 H F O H CF₃ CH₃ COO^(i)C₃H₇ 3-177 H F O H CF₃ CH₃ COCH₃ 3-178 H F O H CF₃ CH₃ COC₂H₅ 3-179 H Cl O H CF₃ CH₃ CH₂Br 3-180 H Cl O H CF₃ CH₃ CHBr₂ 3-181 H Cl O H CF₃ CH₃ CBr₃ 3-182 H Cl O H CF₃ CH₃ CHO 3-183 H Cl O H CF₃ CH₃ CN 3-184 H Cl O H CF₃ CH₃ COOH 3-185 H Cl O H CF₃ CH₃ CH₂OH 3-186 H Cl O H CF₃ CH₃ CH₂OCH₃ 3-187 H Cl O H CF₃ CH₃ CH₂OC₂H₅ 3-188 H Cl O H CF₃ CH₃ CH₂O^(i)C₃H₇ 3-189 H Cl O H CF₃ CH₃ CH₂OCH₂OCH₃ 3-190 H Cl O H CF₃ CH₃ CH₂OCH₂OC₂H₅ 3-191 H Cl O H CF₃ CH₃ CH₂OCOCH₃ 3-192 H Cl O H CF₃ CH₃ CH₂OCOC₂H₅ 3-193 H Cl O H CF₃ CH₃ CH₂OCO^(i)C₃H₇ 3-194 H Cl O H CF₃ CH₃ CH₂OCOCH₂Cl 3-195 H Cl O H CF₃ CH₃ CH₂OCOCCl₃ 3-196 H Cl O H CF₃ CH₃ CH₂OCOCF₃ 3-197 H Cl O H CF₃ CH₃ COOCH₃ 3-198 H Cl O H CF₃ CH₃ COOC₂H₅ 3-199 H Cl O H CF₃ CH₃ COO^(n)C₃H₇ 3-200 H Cl O H CF₃ CH₃ COO^(n)C₄H₉ 3-201 H Cl O H CF₃ CH₃ COO^(n)C₅H₁₁ 3-202 H Cl O H CF₃ CH₃ COO^(i)C₃H₇ 3-203 H Cl O H CF₃ CH₃ COCH₃ 3-204 H Cl O H CF₃ CH₃ COC₂H₅ 3-205 F F O H CF₃ CH₃ CH₂Br 3-206 F F O H CF₃ CH₃ CHBr₂ 3-207 F F O H CF₃ CH₃ CBr₃ 3-208 F F O H CF₃ CH₃ CHO 3-209 F F O H CF₃ CH₃ CN 3-210 F F O H CF₃ CH₃ COOH 3-211 F F O H CF₃ CH₃ CH₂OH 3-212 F F O H CF₃ CH₃ CH₂OCH₃ 3-213 F F O H CF₃ CH₃ CH₂OC₂H₅ 3-214 F F O H CF₃ CH₃ CH₂O^(i)C₃H₇ 3-215 F F O H CF₃ CH₃ CH₂OCH₂OCH₃ 3-216 F F O H CF₃ CH₃ CH₂OCH₂OC₂H₅ 3-217 F F O H CF₃ CH₃ CH₂OCOCH₃ 3-218 F F O H CF₃ CH₃ CH₂OCOC₂H₅ 3-219 F F O H CF₃ CH₃ CH₂OCO^(i)C₃H₇ 3-220 F F O H CF₃ CH₃ CH₂OCOCH₂Cl 3-221 F F O H CF₃ CH₃ CH₂OCOCCl₃ 3-222 F F O H CF₃ CH₃ CH₂OCOCF₃ 3-223 F F O H CF₃ CH₃ COOCH₃ 3-224 F F O H CF₃ CH₃ COOC₂H₅ 3-225 F F O H CF₃ CH₃ COO^(n)C₃H₇ 3-226 F F O H CF₃ CH₃ COO^(n)C₄H₉ 3-227 F F O H CF₃ CH₃ COO^(n)C₅H₁₁ 3-228 F F O H CF₃ CH₃ COO^(i)C₃H₇ 3-229 F F O H CF₃ CH₃ COCH₃ 3-230 F F O H CF₃ CH₃ COC₂H₅ 3-231 F Cl O H CF₃ CH₃ CH₂Br 3-232 F Cl O H CF₃ CH₃ CHBr₂ 3-233 F Cl O H CF₃ CH₃ CBr₃ 3-234 F Cl O H CF₃ CH₃ CHO 3-235 F Cl O H CF₃ CH₃ CN 3-236 F Cl O H CF₃ CH₃ COOH 3-237 F Cl O H CF₃ CH₃ CH₂OH 3-238 F Cl O H CF₃ CH₃ CH₂OCH₃ 3-239 F Cl O H CF₃ CH₃ CH₂OC₂H₅ 3-240 F Cl O H CF₃ CH₃ CH₂O^(i)C₃H₇ 3-241 F Cl O H CF₃ CH₃ CH₂OCH₂OCH₃ 3-242 F Cl O H CF₃ CH₃ CH₂OCH₂OC₂H₅ 3-243 F Cl O H CF₃ CH₃ CH₂OCOCH₃ 3-244 F Cl O H CF₃ CH₃ CH₂OCOC₂H₅ 3-245 F Cl O H CF₃ CH₃ CH₂OCO^(i)C₃H₇ 3-246 F Cl O H CF₃ CH₃ CH₂OCOCH₂Cl 3-247 F Cl O H CF₃ CH₃ CH₂OCOCCl₃ 3-248 F Cl O H CF₃ CH₃ CH₂OCOCF₃ 3-249 F Cl O H CF₃ CH₃ COOCH₃ 3-250 F Cl O H CF₃ CH₃ COOC₂H₅ 3-251 F Cl O H CF₃ CH₃ COO^(n)C₃H₇ 3-252 F Cl O H CF₃ CH₃ COO^(n)C₄H₉ 3-253 F Cl O H CF₃ CH₃ COO^(n)C₅H₁₁ 3-254 F Cl O H CF₃ CH₃ COO^(i)C₃H₇ 3-255 F Cl O H CF₃ CH₃ COCH₃ 3-256 F Cl O H CF₃ CH₃ COC₂H₅ 3-257 H F O H CF₂Cl H CH₂Br 3-258 H F O H CF₂Cl H CHBr₂ 3-259 H F O H CF₂Cl H CBr₃ 3-260 H F O H CF₂Cl H CHO 3-261 H F O H CF₂Cl H CN 3-262 H F O H CF₂Cl H COOH 3-263 H F O H CF₂Cl H CH₂OH 3-264 H F O H CF₂Cl H CH₂OCH₃ 3-265 H F O H CF₂Cl H CH₂OC₂H₅ 3-266 H F O H CF₂Cl H CH₂O^(i)C₃H₇ 3-267 H F O H CF₂Cl H CH₂OCH₂OCH₃ 3-268 H F O H CF₂Cl H CH₂OCH₂OC₂H₅ 3-269 H F O H CF₂Cl H CH₂OCOCH₃ 3-270 H F O H CF₂Cl H CH₂OCOC₂H₅ 3-271 H F O H CF₂Cl H CH₂OCO^(i)C₃H₇ 3-272 H F O H CF₂Cl H CH₂OCOCH₂Cl 3-273 H F O H CF₂Cl H CH₂OCOCCl₃ 3-274 H F O H CF₂Cl H CH₂OCOCF₃ 3-275 H F O H CF₂Cl H COOCH₃ 3-276 H F O H CF₂Cl H COOC₂H₅ 3-277 H F O H CF₂Cl H COO^(n)C₃H₇ 3-278 H F O H CF₂Cl H COO^(n)C₄H₉ 3-279 H F O H CF₂Cl H COO^(n)C₅H₁₁ 3-280 H F O H CF₂Cl H COO^(i)C₃H₇ 3-281 H F O H CF₂Cl H COCH₃ 3-282 H F O H CF₂Cl H COC₂H₅ 3-283 H Cl O H CF₂Cl H CH₂Br 3-284 H Cl O H CF₂Cl H CHBr₂ 3-285 H Cl O H CF₂Cl H CBr₃ 3-286 H Cl O H CF₂Cl H CHO 3-287 H Cl O H CF₂Cl H CN 3-288 H Cl O H CF₂Cl H COOH 3-289 H Cl O H CF₂Cl H CH₂OH 3-290 H Cl O H CF₂Cl H CH₂OCH₃ 3-291 H Cl O H CF₂Cl H CH₂OC₂H₅ 3-292 H Cl O H CF₂Cl H CH₂O^(i)C₃H₇ 3-293 H Cl O H CF₂Cl H CH₂OCH₂OCH₃ 3-294 H Cl O H CF₂Cl H CH₂OCH₂OC₂H₅ 3-295 H Cl O H CF₂Cl H CH₂OCOCH₃ 3-296 H Cl O H CF₂Cl H CH₂OCOC₂H₅ 3-297 H Cl O H CF₂Cl H CH₂OCO^(i)C₃H₇ 3-298 H Cl O H CF₂Cl H CH₂OCOCH₂Cl 3-299 H Cl O H CF₂Cl H CH₂OCOCCl₃ 3-300 H Cl O H CF₂Cl H CH₂OCOCF₃ 3-301 H Cl O H CF₂Cl H COOCH₃ 3-302 H Cl O H CF₂Cl H COOC₂H₅ 3-303 H Cl O H CF₂Cl H COO^(n)C₃H₇ 3-304 H Cl O H CF₂Cl H COO^(n)C₄H₉ 3-305 H Cl O H CF₂Cl H COO^(n)C₅H₁₁ 3-306 H Cl O H CF₂Cl H COO^(i)C₃H₇ 3-307 H Cl O H CF₂Cl H COCH₃ 3-308 H Cl O H CF₂Cl H COC₂H₅ 3-309 F F O H CF₂Cl H CH₂Br 3-310 F F O H CF₂Cl H CHBr₂ 3-311 F F O H CF₂Cl H CBr₃ 3-312 F F O H CF₂Cl H CHO 3-313 F F O H CF₂Cl H CN 3-314 F F O H CF₂Cl H COOH 3-315 F F O H CF₂Cl H CH₂OH 3-316 F F O H CF₂Cl H CH₂OCH₃ 3-317 F F O H CF₂Cl H CH₂OC₂H₅ 3-318 F F O H CF₂Cl H CH₂O^(i)C₃H₇ 3-319 F F O H CF₂Cl H CH₂OCH₂OCH₃ 3-320 F F O H CF₂Cl H CH₂OCH₂OC₂H₅ 3-321 F F O H CF₂Cl H CH₂OCOCH₃ 3-322 F F O H CF₂Cl H CH₂OCOC₂H₅ 3-323 F F O H CF₂Cl H CH₂OCO^(i)C₃H₇ 3-324 F F O H CF₂Cl H CH₂OCOCH₂Cl 3-325 F F O H CF₂Cl H CH₂OCOCCl₃ 3-326 F F O H CF₂Cl H CH₂OCOCF₃ 3-327 F F O H CF₂Cl H COOCH₃ 3-328 F F O H CF₂Cl H COOC₂H₅ 3-329 F F O H CF₂Cl H COO^(n)C₃H₇ 3-330 F F O H CF₂Cl H COO^(n)C₄H₉ 3-331 F F O H CF₂Cl H COO^(n)C₅H₁₁ 3-332 F F O H CF₂Cl H COO^(i)C₃H₇ 3-333 F F O H CF₂Cl H COCH₃ 3-334 F F O H CF₂Cl H COC₂H₅ 3-335 F Cl O H CF₂Cl H CH₂Br 3-336 F Cl O H CF₂Cl H CHBr₂ 3-337 F Cl O H CF₂Cl H CBr₃ 3-338 F Cl O H CF₂Cl H CHO 3-339 F Cl O H CF₂Cl H CN 3-340 F Cl O H CF₂Cl H COOH 3-341 F Cl O H CF₂Cl H CH₂OH 3-342 F Cl O H CF₂Cl H CH₂OCH₃ 3-343 F Cl O H CF₂Cl H CH₂OC₂H₅ 3-344 F Cl O H CF₂Cl H CH₂O^(i)C₃H₇ 3-345 F Cl O H CF₂Cl H CH₂OCH₂OCH₃ 3-346 F Cl O H CF₂Cl H CH₂OCH₂OC₂H₅ 3-347 F Cl O H CF₂Cl H CH₂OCOCH₃ 3-348 F Cl O H CF₂Cl H CH₂OCOC₂H₅ 3-349 F Cl O H CF₂Cl H CH₂OCO^(i)C₃H₇ 3-350 F Cl O H CF₂Cl H CH₂OCOCH₂Cl 3-351 F Cl O H CF₂Cl H CH₂OCOCCl₃ 3-352 F Cl O H CF₂Cl H CH₂OCOCF₃ 3-353 F Cl O H CF₂Cl H COOCH₃ 3-354 F Cl O H CF₂Cl H COOC₂H₅ 3-355 F Cl O H CF₂Cl H COO^(n)C₃H₇ 3-356 F Cl O H CF₂Cl H COO^(n)C₄H₉ 3-357 F Cl O H CF₂Cl H COO^(n)C₅H₁₁ 3-358 F Cl O H CF₂Cl H COO^(i)C₃H₇ 3-359 F Cl O H CF₂Cl H COCH₃ 3-360 F Cl O H CF₂Cl H COC₂H₅ 3-361 F Br O H CF₃ H C₂H₅ 3-362 H F O H CF₃ H CH₂Br 3-363 H F O H CF₃ H CHBr₂ 3-364 H F O H CF₃ H CBr₃ 3-365 H F O H CF₃ H CHO 3-366 H F O H CF₃ H CN 3-367 H F O H CF₃ H COOH 3-368 H F O H CF₃ H CH₂OH 3-369 H F O H CF₃ H CH₂OCH₃ 3-370 H F O H CF₃ H CH₂OC₂H₅ 3-371 H F O H CF₃ H CH₂O^(i)C₃H₇ 3-372 H F O H CF₃ H CH₂OCH₂OCH₃ 3-373 H F O H CF₃ H CH₂OCH₂OC₂H₅ 3-374 H F O H CF₃ H CH₂OCOCH₃ 3-375 H F O H CF₃ H CH₂OCOC₂H₅ 3-376 H F O H CF₃ H CH₂OCO^(i)C₃H₇ 3-377 H F O H CF₃ H CH₂OCOCH₂Cl 3-378 H F O H CF₃ H CH₂OCOCCl₃ 3-379 H F O H CF₃ H CH₂OCOCF₃ 3-380 H F O H CF₃ H COOCH₃ 3-381 H F O H CF₃ H COOC₂H₅ 3-382 H F O H CF₃ H COO^(n)C₃H₇ 3-383 H F O H CF₃ H COO^(n)C₄H₉ 3-384 H F O H CF₃ H COO^(n)C₅H₁₁ 3-385 H F O H CF₃ H COO^(i)C₃H₇ 3-386 H F O H CF₃ H COCH₃ 3-387 H F O H CF₃ H COC₂H₅ 3-388 H Cl O H CF₃ H CH₂Br 3-389 H Cl O H CF₃ H CHBr₂ 3-390 H Cl O H CF₃ H CBr₃ 3-391 H Cl O H CF₃ H CHO 3-392 H Cl O H CF₃ H CN 3-393 H Cl O H CF₃ H COOH 3-394 H Cl O H CF₃ H CH₂OH 3-395 H Cl O H CF₃ H CH₂OCH₃ 3-396 H Cl O H CF₃ H CH₂OC₂H₅ 3-397 H Cl O H CF₃ H CH₂O^(i)C₃H₇ 3-398 H Cl O H CF₃ H CH₂OCH₂OCH₃ 3-399 H Cl O H CF₃ H CH₂OCH₂OC₂H₅ 3-400 H Cl O H CF₃ H CH₂OCOCH₃ 3-401 H Cl O H CF₃ H CH₂OCOC₂H₅ 3-402 H Cl O H CF₃ H CH₂OCO^(i)C₃H₇ 3-403 H Cl O H CF₃ H CH₂OCOCH₂Cl 3-404 H Cl O H CF₃ H CH₂OCOCCl₃ 3-405 H Cl O H CF₃ H CH₂OCOCF₃ 3-406 H Cl O H CF₃ H COOCH₃ 3-407 H Cl O H CF₃ H COOC₂H₅ 3-408 H Cl O H CF₃ H COO^(n)C₃H₇ 3-409 H Cl O H CF₃ H COO^(n)C₄H₉ 3-410 H Cl O H CF₃ H COO^(n)C₅H₁₁ 3-411 H Cl O H CF₃ H COO^(i)C₃H₇ 3-412 H Cl O H CF₃ H COCH₃ 3-413 H Cl O H CF₃ H COC₂H₅ 3-414 F F O H CF₃ H CH₂Br 3-415 F F O H CF₃ H CHBr₂ 3-416 F F O H CF₃ H CBr₃ 3-417 F F O H CF₃ H CHO 3-418 F F O H CF₃ H CN 3-419 F F O H CF₃ H COOH 3-420 F F O H CF₃ H CH₂OH 3-421 F F O H CF₃ H CH₂OCH₃ 3-422 F F O H CF₃ H CH₂OC₂H₅ 3-423 F F O H CF₃ H CH₂O^(i)C₃H₇ 3-424 F F O H CF₃ H CH₂OCH₂OCH₃ 3-425 F F O H CF₃ H CH₂OCH₂OC₂H₅ 3-426 F F O H CF₃ H CH₂OCOCH₃ 3-427 F F O H CF₃ H CH₂OCOC₂H₅ 3-428 F F O H CF₃ H CH₂OCO^(i)C₃H₇ 3-429 F F O H CF₃ H CH₂OCOCH₂Cl 3-430 F F O H CF₃ H CH₂OCOCCl₃ 3-431 F F O H CF₃ H CH₂OCOCF₃ 3-432 F F O H CF₃ H COOCH₃ 3-433 F F O H CF₃ H COOC₂H₅ 3-434 F F O H CF₃ H COO^(n)C₃H₇ 3-435 F F O H CF₃ H COO^(n)C₄H₉ 3-436 F F O H CF₃ H COO^(n)C₅H₁₁ 3-437 F F O H CF₃ H COO^(i)C₃H₇ 3-438 F F O H CF₃ H COCH₃ 3-439 F F O H CF₃ H COC₂H₅ 3-440 F Cl O H CF₃ H CH₂Br 3-441 F Cl O H CF₃ H CHBr₂ 3-442 F Cl O H CF₃ H CBr₃ 3-443 F Cl O H CF₃ H CHO 3-444 F Cl O H CF₃ H CN 3-445 F Cl O H CF₃ H COOH 3-446 F Cl O H CF₃ H CH₂OH 3-447 F Cl O H CF₃ H CH₂OCH₃ 3-448 F Cl O H CF₃ H CH₂OC₂H₅ 3-449 F Cl O H CF₃ H CH₂O^(i)C₃H₇ 3-450 F Cl O H CF₃ H CH₂OCH₂OCH₃ 3-451 F Cl O H CF₃ H CH₂OCH₂OC₂H₅ 3-452 F Cl O H CF₃ H CH₂OCOCH₃ 3-453 F Cl O H CF₃ H CH₂OCOC₂H₅ 3-454 F Cl O H CF₃ H CH₂OCO^(i)C₃H₇ 3-455 F Cl O H CF₃ H CH₂OCOCH₂Cl 3-456 F Cl O H CF₃ H CH₂OCOCCl₃ 3-457 F Cl O H CF₃ H CH₂OCOCF₃ 3-458 F Cl O H CF₃ H COOCH₃ 3-459 F Cl O H CF₃ H COOC₂H₅ 3-460 F Cl O H CF₃ H COO^(n)C₃H₇ 3-461 F Cl O H CF₃ H COO^(n)C₄H₉ 3-462 F Cl O H CF₃ H COO^(n)C₅H₁₁ 3-463 F Cl O H CF₃ H COO^(i)C₃H₇ 3-464 F Cl O H CF₃ H COCH₃ 3-465 F Cl O H CF₃ H COC₂H₅ 3-466 H F O CH₃ CF₃ H CH₃ 3-467 H Cl O CH₃ CF₃ H CH₃ 3-468 H Br O CH₃ CF₃ H CH₃ 3-469 F F O CH₃ CF₃ H CH₃ 3-470 F Cl O CH₃ CF₃ H CH₃ 3-471 F Br O CH₃ CF₃ H CH₃ 3-472 H F O CH₃ CF₃ H C₂H₅ 3-473 H Cl O CH₃ CF₃ H C₂H₅ 3-474 H Br O CH₃ CF₃ H C₂H₅ 3-475 F F O CH₃ CF₃ H C₂H₅ 3-476 F Cl O CH₃ CF₃ H C₂H₅ 3-477 F Br O CH₃ CF₃ H C₂H₅ 3-478 F Br O CH₃ CF₃ H C₂H₅ 3-479 H F O CH₃ CF₃ H CH₂Br 3-480 H F O CH₃ CF₃ H CHBr₂ 3-481 H F O CH₃ CF₃ H CBr₃ 3-482 H F O CH₃ CF₃ H CHO 3-483 H F O CH₃ CF₃ H CN 3-484 H F O CH₃ CF₃ H COOH 3-485 H F O CH₃ CF₃ H CH₂OH 3-486 H F O CH₃ CF₃ H CH₂OCH₃ 3-487 H F O CH₃ CF₃ H CH₂OC₂H₅ 3-488 H F O CH₃ CF₃ H CH₂O^(i)C₃H₇ 3-489 H F O CH₃ CF₃ H CH₂OCH₂OCH₃ 3-490 H F O CH₃ CF₃ H CH₂OCH₂OC₂H₅ 3-491 H F O CH₃ CF₃ H CH₂OCOCH₃ 3-492 H F O CH₃ CF₃ H CH₂OCOC₂H₅ 3-493 H F O CH₃ CF₃ H CH₂OCO^(i)C₃H₇ 3-494 H F O CH₃ CF₃ H CH₂OCOCH₂Cl 3-495 H F O CH₃ CF₃ H CH₂OCOCCl₃ 3-496 H F O CH₃ CF₃ H CH₂OCOCF₃ 3-497 H F O CH₃ CF₃ H COOCH₃ 3-498 H F O CH₃ CF₃ H COOC₂H₅ 3-499 H F O CH₃ CF₃ H COO^(n)C₃H₇ 3-500 H F O CH₃ CF₃ H COO^(n)C₄H₉ 3-501 H F O CH₃ CF₃ H COO^(n)C₅H₁₁ 3-502 H F O CH₃ CF₃ H COO^(i)C₃H₇ 3-503 H F O CH₃ CF₃ H COCH₃ 3-504 H F O CH₃ CF₃ H COC₂H₅ 3-505 H Cl O CH₃ CF₃ H CH₂Br 3-506 H Cl O CH₃ CF₃ H CHBr₂ 3-507 H Cl O CH₃ CF₃ H CBr₃ 3-508 H Cl O CH₃ CF₃ H CHO 3-509 H Cl O CH₃ CF₃ H CN 3-510 H Cl O CH₃ CF₃ H COOH 3-511 H Cl O CH₃ CF₃ H CH₂OH 3-512 H Cl O CH₃ CF₃ H CH₂OCH₃ 3-513 H Cl O CH₃ CF₃ H CH₂OC₂H₅ 3-514 H Cl O CH₃ CF₃ H CH₂O^(i)C₃H₇ 3-515 H Cl O CH₃ CF₃ H CH₂OCH₂OCH₃ 3-516 H Cl O CH₃ CF₃ H CH₂OCH₂OC₂H₅ 3-517 H Cl O CH₃ CF₃ H CH₂OCOCH₃ 3-518 H Cl O CH₃ CF₃ H CH₂OCOC₂H₅ 3-519 H Cl O CH₃ CF₃ H CH₂OCO^(i)C₃H₇ 3-520 H Cl O CH₃ CF₃ H CH₂OCOCH₂Cl 3-521 H Cl O CH₃ CF₃ H CH₂OCOCCl₃ 3-522 H Cl O CH₃ CF₃ H CH₂OCOCF₃ 3-523 H Cl O CH₃ CF₃ H COOCH₃ 3-524 H Cl O CH₃ CF₃ H COOC₂H₅ 3-525 H Cl O CH₃ CF₃ H COO^(n)C₃H₇ 3-526 H Cl O CH₃ CF₃ H COO^(n)C₄H₉ 3-527 H Cl O CH₃ CF₃ H COO^(n)C₅H₁₁ 3-528 H Cl O CH₃ CF₃ H COO^(i)C₃H₇ 3-529 H Cl O CH₃ CF₃ H COCH₃ 3-530 H Cl O CH₃ CF₃ H COC₂H₅ 3-531 F F O CH₃ CF₃ H CH₂Br 3-532 F F O CH₃ CF₃ H CHBr₂ 3-533 F F O CH₃ CF₃ H CBr₃ 3-534 F F O CH₃ CF₃ H CHO 3-535 F F O CH₃ CF₃ H CN 3-536 F F O CH₃ CF₃ H COOH 3-537 F F O CH₃ CF₃ H CH₂OH 3-538 F F O CH₃ CF₃ H CH₂OCH₃ 3-539 F F O CH₃ CF₃ H CH₂OC₂H₅ 3-540 F F O CH₃ CF₃ H CH₂O^(i)C₃H₇ 3-541 F F O CH₃ CF₃ H CH₂OCH₂OCH₃ 3-542 F F O CH₃ CF₃ H CH₂OCH₂OC₂H₅ 3-543 F F O CH₃ CF₃ H CH₂OCOCH₃ 3-544 F F O CH₃ CF₃ H CH₂OCOC₂H₅ 3-545 F F O CH₃ CF₃ H CH₂OCO^(i)C₃H₇ 3-546 F F O CH₃ CF₃ H CH₂OCOCH₂Cl 3-547 F F O CH₃ CF₃ H CH₂OCOCCl₃ 3-548 F F O CH₃ CF₃ H CH₂OCOCF₃ 3-549 F F O CH₃ CF₃ H COOCH₃ 3-550 F F O CH₃ CF₃ H COOC₂H₅ 3-551 F F O CH₃ CF₃ H COO^(n)C₃H₇ 3-552 F F O CH₃ CF₃ H COO^(n)C₄H₉ 3-553 F F O CH₃ CF₃ H COO^(n)C₅H₁₁ 3-554 F F O CH₃ CF₃ H COO^(i)C₃H₇ 3-555 F F O CH₃ CF₃ H COCH₃ 3-556 F F O CH₃ CF₃ H COC₂H₅ 3-557 F Cl O CH₃ CF₃ H CH₂Br 3-558 F Cl O CH₃ CF₃ H CHBr₂ 3-559 F Cl O CH₃ CF₃ H CBr₃ 3-560 F Cl O CH₃ CF₃ H CHO 3-561 F Cl O CH₃ CF₃ H CN 3-562 F Cl O CH₃ CF₃ H COOH 3-563 F Cl O CH₃ CF₃ H CH₂OH 3-564 F Cl O CH₃ CF₃ H CH₂OCH₃ 3-565 F Cl O CH₃ CF₃ H CH₂OC₂H₅ 3-566 F Cl O CH₃ CF₃ H CH₂O^(i)C₃H₇ 3-567 F Cl O CH₃ CF₃ H CH₂OCH₂OCH₃ 3-568 F Cl O CH₃ CF₃ H CH₂OCH₂OC₂H₅ 3-569 F Cl O CH₃ CF₃ H CH₂OCOCH₃ 3-570 F Cl O CH₃ CF₃ H CH₂OCOC₂H₅ 3-571 F Cl O CH₃ CF₃ H CH₂OCO^(i)C₃H₇ 3-572 F Cl O CH₃ CF₃ H CH₂OCOCH₂Cl 3-573 F Cl O CH₃ CF₃ H CH₂OCOCCl₃ 3-574 F Cl O CH₃ CF₃ H CH₂OCOCF₃ 3-575 F Cl O CH₃ CF₃ H COOCH₃ 3-576 F Cl O CH₃ CF₃ H COOC₂H₅ 3-577 F Cl O CH₃ CF₃ H COO^(n)C₃H₇ 3-578 F Cl O CH₃ CF₃ H COO^(n)C₄H₉ 3-579 F Cl O CH₃ CF₃ H COO^(n)C₅H₁₁ 3-580 F Cl O CH₃ CF₃ H COO^(i)C₃H₇ 3-581 F Cl O CH₃ CF₃ H COCH₃ 3-582 F Cl O CH₃ CF₃ H COC₂H₅

TABLE 4 Compounds of the formula:

Com- pound No. X Y R³ R¹ R² R⁷ R⁸ 4-1  H Cl H CF₂Cl CH₃ H CH₂Cl 4-2  H Cl H CF₂Cl CH₃ H CH₂Br 4-3  H Cl H CF₂Cl CH₃ H CH₂OCH₃ 4-4  H Cl H CF₂Cl CH₃ H CH₂OC₂H₅ 4-5  H Cl H CF₂Cl CH₃ H CH₂OCH₂OCH₃ 4-6  H Cl H CF₂Cl CH₃ H CH₂OCH₂OC₂H₅ 4-7  H Cl H CF₂Cl CH₃ H CH₂OCOCH₃ 4-8  H Cl H CF₂Cl CH₃ H CH₂OCOC₂H₅ 4-9  H Cl H CF₂Cl CH₃ H CH₂OCO^(i)C₃H₇ 4-10  H Cl H CF₂Cl CH₃ H CH₂OCOCH₂Cl 4-11  H Cl H CF₂Cl CH₃ H CH₂OCOCCl₃ 4-12  H Cl H CF₂Cl CH₃ H CH₂OCOCF₃ 4-13  H Cl H CF₂Cl CH₃ H COOH 4-14  H Cl H CF₂Cl CH₃ H COOCH₃ 4-15  H Cl H CF₂Cl CH₃ H COOC₂H₅ 4-16  H Cl H CF₂Cl CH₃ H COO^(n)C₃H₇ 4-17  H Cl H CF₂Cl CH₃ H COO^(n)C₄H₉ 4-18  H Cl H CF₂Cl CH₃ H COO^(n)C₅H₁₁ 4-19  H Cl H CF₂Cl CH₃ H COO^(i)C₃H₇ 4-20  H Cl H CF₂Cl CH₃ H COO^(c)C₅H₉ 4-21  H Cl H CF₂Cl CH₃ H COO^(c)C₆H₁₁ 4-22  H Cl H CF₂Cl CH₃ H COOCH₂CH═CH₂ 4-23  H Cl H CF₂Cl CH₃ H COOCH₂C≡CH 4-24  H Cl H CF₂Cl CH₃ H CONH₂ 4-25  H Cl H CF₂Cl CH₃ H CONHCH₃ 4-26  H Cl H CF₂Cl CH₃ H CONHC₂H₅ 4-27  H Cl H CF₂Cl CH₃ H CON(CH₃)₂ 4-28  H Cl H CF₂Cl CH₃ H CON(C₂H₅)₂ 4-29  F Cl H CF₂Cl CH₃ H CH₂Cl 4-30  F Cl H CF₂Cl CH₃ H CH₂Br 4-31  F Cl H CF₂Cl CH₃ H CH₂OCH₃ 4-32  F Cl H CF₂Cl CH₃ H CH₂OC₂H₅ 4-33  F Cl H CF₂Cl CH₃ H CH₂OCH₂OCH₃ 4-34  F Cl H CF₂Cl CH₃ H CH₂OCH₂OC₂H₅ 4-35  F Cl H CF₂Cl CH₃ H CH₂OCOCH₃ 4-36  F Cl H CF₂Cl CH₃ H CH₂OCOC₂H₅ 4-37  F Cl H CF₂Cl CH₃ H CH₂OCO^(i)C₃H₇ 4-38  F Cl H CF₂Cl CH₃ H CH₂OCOCH₂Cl 4-39  F Cl H CF₂Cl CH₃ H CH₂OCOCCl₃ 4-40  F Cl H CF₂Cl CH₃ H CH₂OCOCF₃ 4-41  F Cl H CF₂Cl CH₃ H COOH 4-42  F Cl H CF₂Cl CH₃ H COOCH₃ 4-43  F Cl H CF₂Cl CH₃ H COOC₂H₅ 4-44  F Cl H CF₂Cl CH₃ H COO^(n)C₃H₇ 4-45  F Cl H CF₂Cl CH₃ H COO^(n)C₄H₉ 4-46  F Cl H CF₂Cl CH₃ H COO^(n)C₅H₁₁ 4-47  F Cl H CF₂Cl CH₃ H COO^(i)C₃H₇ 4-48  F Cl H CF₂Cl CH₃ H COO^(c)C₅H₉ 4-49  F Cl H CF₂Cl CH₃ H COO^(c)C₆H₁₁ 4-50  F Cl H CF₂Cl CH₃ H COOCH₂CH═CH₂ 4-51  F Cl H CF₂Cl CH₃ H COOCH₂C≡CH 4-52  F Cl H CF₂Cl CH₃ H CONH₂ 4-53  F Cl H CF₂Cl CH₃ H CONHCH₃ 4-54  F Cl H CF₂Cl CH₃ H CONHC₂H₅ 4-55  F Cl H CF₂Cl CH₃ H CON(CH₃)₂ 4-56  F Cl H CF₂Cl CH₃ H CON(C₂H₅)₂ 4-57  H Cl H CF₂Cl CH₃ CH₃ CH₂Cl 4-58  H Cl H CF₂Cl CH₃ CH₃ CH₂Br 4-59  H Cl H CF₂Cl CH₃ CH₃ CH₂OCH₃ 4-60  H Cl H CF₂Cl CH₃ CH₃ CH₂OC₂H₅ 4-61  H Cl H CF₂Cl CH₃ CH₃ CH₂OCH₂OCH₃ 4-62  H Cl H CF₂Cl CH₃ CH₃ CH₂OCH₂OC₂H₅ 4-63  H Cl H CF₂Cl CH₃ CH₃ CH₂OCOCH₃ 4-64  H Cl H CF₂Cl CH₃ CH₃ CH₂OCOC₂H₅ 4-65  H Cl H CF₂Cl CH₃ CH₃ CH₂OCO^(i)C₃H₇ 4-66  H Cl H CF₂Cl CH₃ CH₃ CH₂OCOCH₂Cl 4-67  H Cl H CF₂Cl CH₃ CH₃ CH₂OCOCCl₃ 4-68  H Cl H CF₂Cl CH₃ CH₃ CH₂OCOCF₃ 4-69  H Cl H CF₂Cl CH₃ CH₃ COOH 4-70  H Cl H CF₂Cl CH₃ CH₃ COOCH₃ 4-71  H Cl H CF₂Cl CH₃ CH₃ COOC₂H₅ 4-72  H Cl H CF₂Cl CH₃ CH₃ COO^(n)C₃H₇ 4-73  H Cl H CF₂Cl CH₃ CH₃ COO^(n)C₄H₉ 4-74  H Cl H CF₂Cl CH₃ CH₃ COO^(n)C₅H₁₁ 4-75  H Cl H CF₂Cl CH₃ CH₃ COO^(i)C₃H₇ 4-76  H Cl H CF₂Cl CH₃ CH₃ COO^(c)C₅H₉ 4-77  H Cl H CF₂Cl CH₃ CH₃ COO^(c)C₅H₁₁ 4-78  H Cl H CF₂Cl CH₃ CH₃ COOCH₂CH═CH₂ 4-79  H Cl H CF₂Cl CH₃ CH₃ COOCH₂C≡CH 4-80  H Cl H CF₂Cl CH₃ CH₃ CONH₂ 4-81  H Cl H CF₂Cl CH₃ CH₃ CONHCH₃ 4-82  H Cl H CF₂Cl CH₃ CH₃ CONHC₂H₅ 4-83  H Cl H CF₂Cl CH₃ CH₃ CON(CH₃)₂ 4-84  H Cl H CF₂Cl CH₃ CH₃ CON(C₂H₅)₂ 4-85  F Cl H CF₂Cl CH₃ CH₃ CH₂Cl 4-86  F Cl H CF₂Cl CH₃ CH₃ CH₂Br 4-87  F Cl H CF₂Cl CH₃ CH₃ CH₂OCH₃ 4-88  F Cl H CF₂Cl CH₃ CH₃ CH₂OC₂H₅ 4-89  F Cl H CF₂Cl CH₃ CH₃ CH₂OCH₂OCH₃ 4-90  F Cl H CF₂Cl CH₃ CH₃ CH₂OCH₂OC₂H₅ 4-91  F Cl H CF₂Cl CH₃ CH₃ CH₂OCOCH₃ 4-92  F Cl H CF₂Cl CH₃ CH₃ CH₂OCOC₂H₅ 4-93  F Cl H CF₂Cl CH₃ CH₃ CH₂OCO^(i)C₃H₇ 4-94  F Cl H CF₂Cl CH₃ CH₃ CH₂OCOCH₂Cl 4-95  F Cl H CF₂Cl CH₃ CH₃ CH₂OCOCCl₃ 4-96  F Cl H CF₂Cl CH₃ CH₃ CH₂OCOCF₃ 4-97  F Cl H CF₂Cl CH₃ CH₃ COOH 4-98  F Cl H CF₂Cl CH₃ CH₃ COOCH₃ 4-99  F Cl H CF₂Cl CH₃ CH₃ COOC₂H₅ 4-100 F Cl H CF₂Cl CH₃ CH₃ COO^(n)C₃H₇ 4-101 F Cl H CF₂Cl CH₃ CH₃ COO^(n)C₄H₉ 4-102 F Cl H CF₂Cl CH₃ CH₃ COO^(n)C₅H₁₁ 4-103 F Cl H CF₂Cl CH₃ CH₃ COO^(i)C₃H₇ 4-104 F Cl H CF₂Cl CH₃ CH₃ COO^(c)C₅H₉ 4-105 F Cl H CF₂Cl CH₃ CH₃ COO^(c)C₆H₁₁ 4-106 F Cl H CF₂Cl CH₃ CH₃ COOCH₂CH═CH₂ 4-107 F Cl H CF₂Cl CH₃ CH₃ COOCH₂C≡CH 4-108 F Cl H CF₂Cl CH₃ CH₃ CONH₂ 4-109 F Cl H CF₂Cl CH₃ CH₃ CONHCH₃ 4-110 F Cl H CF₂Cl CH₃ CH₃ CONHC₂H₅ 4-111 F Cl H CF₂Cl CH₃ CH₃ CON(CH₃)₂ 4-112 F Cl H CF₂Cl CH₃ CH₃ CON(C₂H₅)₂ 4-113 H Cl H CF₃ CH₃ H CH₂Cl 4-114 H Cl H CF₃ CH₃ H CH₂Br 4-115 H Cl H CF₃ CH₃ H CH₂OCH₃ 4-116 H Cl H CF₃ CH₃ H CH₂OC₂H₅ 4-117 H Cl H CF₃ CH₃ H CH₂OCH₂OCH₃ 4-118 H Cl H CF₃ CH₃ H CH₂OCH₂OC₂H₅ 4-119 H Cl H CF₃ CH₃ H CH₂OCOCH₃ 4-120 H Cl H CF₃ CH₃ H CH₂OCOC₂H₅ 4-121 H Cl H CF₃ CH₃ H CH₂OCO^(i)C₃H₇ 4-122 H Cl H CF₃ CH₃ H CH₂OCOCH₂Cl 4-123 H Cl H CF₃ CH₃ H CH₂OCOCCl₃ 4-124 H Cl H CF₃ CH₃ H CH₂OCOCF₃ 4-125 H Cl H CF₃ CH₃ H COOH 4-126 H Cl H CF₃ CH₃ H COOCH₃ 4-127 H Cl H CF₃ CH₃ H COOC₂H₅ 4-128 H Cl H CF₃ CH₃ H COO^(n)C₃H₇ 4-129 H Cl H CF₃ CH₃ H COO^(n)C₄H₉ 4-130 H Cl H CF₃ CH₃ H COO^(n)C₅H₁₁ 4-131 H Cl H CF₃ CH₃ H COO^(i)C₃H₇ 4-132 H Cl H CF₃ CH₃ H COO^(c)C₅H₉ 4-133 H Cl H CF₃ CH₃ H COO^(c)C₆H₁₁ 4-134 H Cl H CF₃ CH₃ H COOCH₂CH═CH₂ 4-135 H Cl H CF₃ CH₃ H COOCH₂C≡CH 4-136 H Cl H CF₃ CH₃ H CONH₂ 4-137 H Cl H CF₃ CH₃ H CONHCH₃ 4-138 H Cl H CF₃ CH₃ H CONHC₂H₅ 4-139 H Cl H CF₃ CH₃ H CON(CH₃)₂ 4-140 H Cl H CF₃ CH₃ H CON(C₂H₅)₂ 4-141 F Cl H CF₃ CH₃ H CH₂Cl 4-142 F Cl H CF₃ CH₃ H CH₂Br 4-143 F Cl H CF₃ CH₃ H CH₂OCH₃ 4-144 F Cl H CF₃ CH₃ H CH₂OC₂H₅ 4-145 F Cl H CF₃ CH₃ H CH₂OCH₂OCH₃ 4-146 F Cl H CF₃ CH₃ H CH₂OCH₂OC₂H₅ 4-147 F Cl H CF₃ CH₃ H CH₂OCOCH₃ 4-148 F Cl H CF₃ CH₃ H CH₂OCOC₂H₅ 4-149 F Cl H CF₃ CH₃ H CH₂OCO^(i)C₃H₇ 4-150 F Cl H CF₃ CH₃ H CH₂OCOCH₂Cl 4-151 F Cl H CF₃ CH₃ H CH₂OCOCCl₃ 4-152 F Cl H CF₃ CH₃ H CH₂OCOCF₃ 4-153 F Cl H CF₃ CH₃ H COOH 4-154 F Cl H CF₃ CH₃ H COOCH₃ 4-155 F Cl H CF₃ CH₃ H COOC₂H₅ 4-156 F Cl H CF₃ CH₃ H COO^(n)C₃H₇ 4-157 F Cl H CF₃ CH₃ H COO^(n)C₄H₉ 4-158 F Cl H CF₃ CH₃ H COO^(n)C₅H₁₁ 4-159 F Cl H CF₃ CH₃ H COO^(i)C₃H₇ 4-160 F Cl H CF₃ CH₃ H COO^(c)C₅H₉ 4-161 F Cl H CF₃ CH₃ H COO^(c)C₆H₁₁ 4-162 F Cl H CF₃ CH₃ H COOCH₂CH═CH₂ 4-163 F Cl H CF₃ CH₃ H COOCH₂C≡CH 4-164 F Cl H CF₃ CH₃ H CONH₂ 4-165 F Cl H CF₃ CH₃ H CONHCH₃ 4-166 F Cl H CF₃ CH₃ H CONHC₂H₅ 4-167 F Cl H CF₃ CH₃ H CON(CH₃)₂ 4-168 F Cl H CF₃ CH₃ H CON(C₂H₅)₂ 4-169 H Cl H CF₃ CH₃ CH₃ CH₂Cl 4-170 H Cl H CF₃ CH₃ CH₃ CH₂Br 4-171 H Cl H CF₃ CH₃ CH₃ CH₂OCH₃ 4-172 H Cl H CF₃ CH₃ CH₃ CH₂OC₂H₅ 4-173 H Cl H CF₃ CH₃ CH₃ CH₂OCH₂OCH₃ 4-174 H Cl H CF₃ CH₃ CH₃ CH₂OCH₂OC₂H₅ 4-175 H Cl H CF₃ CH₃ CH₃ CH₂OCOCH₃ 4-176 H Cl H CF₃ CH₃ CH₃ CH₂OCOC₂H₅ 4-177 H Cl H CF₃ CH₃ CH₃ CH₂OCO^(i)C₃H₇ 4-178 H Cl H CF₃ CH₃ CH₃ CH₂OCOCH₂Cl 4-179 H Cl H CF₃ CH₃ CH₃ CH₂OCOCCl₃ 4-180 H Cl H CF₃ CH₃ CH₃ CH₂OCOCF₃ 4-181 H Cl H CF₃ CH₃ CH₃ COOH 4-182 H Cl H CF₃ CH₃ CH₃ COOCH₃ 4-183 H Cl H CF₃ CH₃ CH₃ COOC₂H₅ 4-184 H Cl H CF₃ CH₃ CH₃ COO^(n)C₃H₇ 4-185 H Cl H CF₃ CH₃ CH₃ COO^(n)C₄H₉ 4-186 H Cl H CF₃ CH₃ CH₃ COO^(n)C₅H₁₁ 4-187 H Cl H CF₃ CH₃ CH₃ COO^(i)C₃H₇ 4-188 H Cl H CF₃ CH₃ CH₃ COO^(c)C₅H₉ 4-189 H Cl H CF₃ CH₃ CH₃ COO^(c)C₆H₁₁ 4-190 H Cl H CF₃ CH₃ CH₃ COOCH₂CH═CH₂ 4-191 H Cl H CF₃ CH₃ CH₃ COOCH₂C≡CH 4-192 H Cl H CF₃ CH₃ CH₃ CONH₂ 4-193 H Cl H CF₃ CH₃ CH₃ CONHCH₃ 4-194 H Cl H CF₃ CH₃ CH₃ CONHC₂H₅ 4-195 H Cl H CF₃ CH₃ CH₃ CON(CH₃)₂ 4-196 H Cl H CF₃ CH₃ CH₃ CON(C₂H₅)₂ 4-197 F Cl H CF₃ CH₃ CH₃ CH₂Cl 4-198 F Cl H CF₃ CH₃ CH₃ CH₂Br 4-199 F Cl H CF₃ CH₃ CH₃ CH₂OCH₃ 4-200 F Cl H CF₃ CH₃ CH₃ CH₂OC₂H₅ 4-201 F Cl H CF₃ CH₃ CH₃ CH₂OCH₂OCH₃ 4-202 F Cl H CF₃ CH₃ CH₃ CH₂OCH₂OC₂H₅ 4-203 F Cl H CF₃ CH₃ CH₃ CH₂OCOCH₃ 4-204 F Cl H CF₃ CH₃ CH₃ CH₂OCOC₂H₅ 4-205 F Cl H CF₃ CH₃ CH₃ CH₂OCO^(i)C₃H₇ 4-206 F Cl H CF₃ CH₃ CH₃ CH₂OCOCH₂Cl 4-207 F Cl H CF₃ CH₃ CH₃ CH₂OCOCCl₃ 4-208 F Cl H CF₃ CH₃ CH₃ CH₂OCOCF₃ 4-209 F Cl H CF₃ CH₃ CH₃ COOH 4-210 F Cl H CF₃ CH₃ CH₃ COOCH₃ 4-211 F Cl H CF₃ CH₃ CH₃ COOC₂H₅ 4-212 F Cl H CF₃ CH₃ CH₃ COO^(n)C₃H₇ 4-213 F Cl H CF₃ CH₃ CH₃ COO^(n)C₄H₉ 4-214 F Cl H CF₃ CH₃ CH₃ COO^(n)C₅H₁₁ 4-215 F Cl H CF₃ CH₃ CH₃ COO^(i)C₃H₇ 4-216 F Cl H CF₃ CH₃ CH₃ COO^(c)C₅H₉ 4-217 F Cl H CF₃ CH₃ CH₃ COO^(c)C₆H₁₁ 4-218 F Cl H CF₃ CH₃ CH₃ COOCH₂CH═CH₂ 4-219 F Cl H CF₃ CH₃ CH₃ COOCH₂C≡CH 4-220 F Cl H CF₃ CH₃ CH₃ CONH₂ 4-221 F Cl H CF₃ CH₃ CH₃ CONHCH₃ 4-222 F Cl H CF₃ CH₃ CH₃ CONHC₂H₅ 4-223 F Cl H CF₃ CH₃ CH₃ CON(CH₃)₂ 4-224 F Cl H CF₃ CH₃ CH₃ CON(C₂H₅)₂ 4-225 H Cl H CF₂Cl CH₃ H CH₂Cl 4-226 H Cl H CF₂Cl CH₃ H CH₂Br 4-227 H Cl H CF₂Cl CH₃ H CH₂OCH₃ 4-228 H Cl H CF₂Cl CH₃ H CH₂OC₂H₅ 4-229 H Cl H CF₂Cl CH₃ H CH₂OCH₂OCH₃ 4-230 H Cl H CF₂Cl CH₃ H CH₂OCH₂OC₂H₅ 4-231 H Cl H CF₂Cl CH₃ H CH₂OCOCH₃ 4-232 H Cl H CF₂Cl CH₃ H CH₂OCOC₂H₅ 4-233 H Cl H CF₂Cl CH₃ H CH₂OCO^(i)C₃H₇ 4-234 H Cl H CF₂Cl CH₃ H CH₂OCOCH₂Cl 4-235 H Cl H CF₂Cl CH₃ H CH₂OCOCCl₃ 4-236 H Cl H CF₂Cl CH₃ H CH₂OCOCF₃ 4-237 H Cl H CF₂Cl CH₃ H COOH 4-238 H Cl H CF₂Cl CH₃ H COOCH₃ 4-239 H Cl H CF₂Cl CH₃ H COOC₂H₅ 4-240 H Cl H CF₂Cl CH₃ H COO^(n)C₃H₇ 4-241 H Cl H CF₂Cl CH₃ H COO^(n)C₄H₉ 4-242 H Cl H CF₂Cl CH₃ H COO^(n)C₅H₁₁ 4-243 H Cl H CF₂Cl CH₃ H COO^(i)C₃H₇ 4-244 H Cl H CF₂Cl CH₃ H COO^(c)C₅H₉ 4-245 H Cl H CF₂Cl CH₃ H COO^(c)C₆H₁₁ 4-246 H Cl H CF₂Cl CH₃ H COOCH₂CH═CH₂ 4-247 H Cl H CF₂Cl CH₃ H COOCH₂C≡CH 4-248 H Cl H CF₂Cl CH₃ H CONH₂ 4-249 H Cl H CF₂Cl CH₃ H CONHCH₃ 4-250 H Cl H CF₂Cl CH₃ H CONHC₂H₅ 4-251 H Cl H CF₂Cl CH₃ H CON(CH₃)₂ 4-252 H Cl H CF₂Cl CH₃ H CON(C₂H₅)₂ 4-253 F Cl H CF₂Cl CH₃ H CH₂Cl 4-254 F Cl H CF₂Cl CH₃ H CH₂Br 4-255 F Cl H CF₂Cl CH₃ H CH₂OCH₃ 4-256 F Cl H CF₂Cl CH₃ H CH₂OC₂H₅ 4-257 F Cl H CF₂Cl CH₃ H CH₂OCH₂OCH₃ 4-258 F Cl H CF₂Cl CH₃ H CH₂OCH₂OC₂H₅ 4-259 F Cl H CF₂Cl CH₃ H CH₂OCOCH₃ 4-260 F Cl H CF₂Cl CH₃ H CH₂OCOC₂H₅ 4-261 F Cl H CF₂Cl CH₃ H CH₂OCO^(i)C₃H₇ 4-262 F Cl H CF₂Cl CH₃ H CH₂OCOCH₂Cl 4-263 F Cl H CF₂Cl CH₃ H CH₂OCOCCl₃ 4-264 F Cl H CF₂Cl CH₃ H CH₂OCOCF₃ 4-265 F Cl H CF₂Cl CH₃ H COOH 4-266 F Cl H CF₂Cl CH₃ H COOCH₃ 4-267 F Cl H CF₂Cl CH₃ H COOC₂H₅ 4-268 F Cl H CF₂Cl CH₃ H COO^(n)C₃H₇ 4-269 F Cl H CF₂Cl CH₃ H COO^(n)C₄H₉ 4-270 F Cl H CF₂Cl CH₃ H COO^(n)C₅H₁₁ 4-271 F Cl H CF₂Cl CH₃ H COO^(i)C₃H₇ 4-272 F Cl H CF₂Cl CH₃ H COO^(c)C₅H₉ 4-273 F Cl H CF₂Cl CH₃ H COO^(c)C₆H₁₁ 4-274 F Cl H CF₂Cl CH₃ H COOCH₂CH═CH₂ 4-275 F Cl H CF₂Cl CH₃ H COOCH₂C≡CH 4-276 F Cl H CF₂Cl CH₃ H CONH₂ 4-277 F Cl H CF₂Cl CH₃ H CONHCH₃ 4-278 F Cl H CF₂Cl CH₃ H CONHC₂H₅ 4-279 F Cl H CF₂Cl CH₃ H CON(CH₃)₂ 4-280 F Cl H CF₂Cl CH₃ H CON(C₂H₅)₂ 4-281 H Cl H CF₂Cl CH₃ CH₃ CH₂Cl 4-282 H Cl H CF₂Cl CH₃ CH₃ CH₂Br 4-283 H Cl H CF₂Cl CH₃ CH₃ CH₂OCH₃ 4-284 H Cl H CF₂Cl CH₃ CH₃ CH₂OC₂H₅ 4-285 H Cl H CF₂Cl CH₃ CH₃ CH₂OCH₂OCH₃ 4-286 H Cl H CF₂Cl CH₃ CH₃ CH₂OCH₂OC₂H₅ 4-287 H Cl H CF₂Cl CH₃ CH₃ CH₂OCOCH₃ 4-288 H Cl H CF₂Cl CH₃ CH₃ CH₂OCOC₂H₅ 4-289 H Cl H CF₂Cl CH₃ CH₃ CH₂OCO^(i)C₃H₇ 4-290 H Cl H CF₂Cl CH₃ CH₃ CH₂OCOCH₂Cl 4-291 H Cl H CF₂Cl CH₃ CH₃ CH₂OCOCCl₃ 4-292 H Cl H CF₂Cl CH₃ CH₃ CH₂OCOCF₃ 4-293 H Cl H CF₂Cl CH₃ CH₃ COOH 4-294 H Cl H CF₂Cl CH₃ CH₃ COOCH₃ 4-295 H Cl H CF₂Cl CH₃ CH₃ COOC₂H₅ 4-296 H Cl H CF₂Cl CH₃ CH₃ COO^(n)C₃H₇ 4-297 H Cl H CF₂Cl CH₃ CH₃ COO^(n)C₄H₉ 4-298 H Cl H CF₂Cl CH₃ CH₃ COO^(n)C₅H₁₁ 4-299 H Cl H CF₂Cl CH₃ CH₃ COO^(i)C₃H₇ 4-300 H Cl H CF₂Cl CH₃ CH₃ COO^(c)C₅H₉ 4-301 H Cl H CF₂Cl CH₃ CH₃ COO^(c)C₆H₁₁ 4-302 H Cl H CF₂Cl CH₃ CH₃ COOCH₂CH═CH₂ 4-303 H Cl H CF₂Cl CH₃ CH₃ COOCH₂C≡CH 4-304 H Cl H CF₂Cl CH₃ CH₃ CONH₂ 4-305 H Cl H CF₂Cl CH₃ CH₃ CONHCH₃ 4-306 H Cl H CF₂Cl CH₃ CH₃ CONHC₂H₅ 4-307 H Cl H CF₂Cl CH₃ CH₃ CON(CH₃)₂ 4-308 H Cl H CF₂Cl CH₃ CH₃ CON(C₂H₅)₂ 4-309 F Cl H CF₂Cl CH₃ CH₃ CH₂Cl 4-310 F Cl H CF₂Cl CH₃ CH₃ CH₂Br 4-311 F Cl H CF₂Cl CH₃ CH₃ CH₂OCH₃ 4-312 F Cl H CF₂Cl CH₃ CH₃ CH₂OC₂H₅ 4-313 F Cl H CF₂Cl CH₃ CH₃ CH₂OCH₂OCH₃ 4-314 F Cl H CF₂Cl CH₃ CH₃ CH₂OCH₂OC₂H₅ 4-315 F Cl H CF₂Cl CH₃ CH₃ CH₂OCOCH₃ 4-316 F Cl H CF₂Cl CH₃ CH₃ CH₂OCOC₂H₅ 4-317 F Cl H CF₂Cl CH₃ CH₃ CH₂OCO^(i)C₃H₇ 4-318 F Cl H CF₂Cl CH₃ CH₃ CH₂OCOCH₂Cl 4-319 F Cl H CF₂Cl CH₃ CH₃ CH₂OCOCCl₃ 4-320 F Cl H CF₂Cl CH₃ CH₃ CH₂OCOCF₃ 4-321 F Cl H CF₂Cl CH₃ CH₃ COOH 4-322 F Cl H CF₂Cl CH₃ CH₃ COOCH₃ 4-323 F Cl H CF₂Cl CH₃ CH₃ COOC₂H₅ 4-324 F Cl H CF₂Cl CH₃ CH₃ COO^(n)C₃H₇ 4-325 F Cl H CF₂Cl CH₃ CH₃ COO^(n)C₄H₉ 4-326 F Cl H CF₂Cl CH₃ CH₃ COO^(n)C₅H₁₁ 4-327 F Cl H CF₂Cl CH₃ CH₃ COO^(i)C₃H₇ 4-328 F Cl H CF₂Cl CH₃ CH₃ COO^(c)C₅H₉ 4-329 F Cl H CF₂Cl CH₃ CH₃ COO^(c)C₆H₁₁ 4-330 F Cl H CF₂Cl CH₃ CH₃ COOCH₂CH═CH₂ 4-331 F Cl H CF₂Cl CH₃ CH₃ COOCH₂C≡CH 4-332 F Cl H CF₂Cl CH₃ CH₃ CONH₂ 4-333 F Cl H CF₂Cl CH₃ CH₃ CONHCH₃ 4-334 F Cl H CF₂Cl CH₃ CH₃ CONHC₂H₅ 4-335 F Cl H CF₂Cl CH₃ CH₃ CON(CH₃)₂ 4-336 F Cl H CF₂Cl CH₃ CH₃ CON(C₂H₅)₂ 4-337 H Cl H CF₃ CH₃ H CH₂Cl 4-338 H Cl H CF₃ CH₃ H CH₂Br 4-339 H Cl H CF₃ CH₃ H CH₂OCH₃ 4-340 H Cl H CF₃ CH₃ H CH₂OC₂H₅ 4-341 H Cl H CF₃ CH₃ H CH₂OCH₂OCH₃ 4-342 H Cl H CF₃ CH₃ H CH₂OCH₂OC₂H₅ 4-343 H Cl H CF₃ CH₃ H CH₂OCOCH₃ 4-344 H Cl H CF₃ CH₃ H CH₂OCOC₂H₅ 4-345 H Cl H CF₃ CH₃ H CH₂OCO^(i)C₃H₇ 4-346 H Cl H CF₃ CH₃ H CH₂OCOCH₂Cl 4-347 H Cl H CF₃ CH₃ H CH₂OCOCCl₃ 4-348 H Cl H CF₃ CH₃ H CH₂OCOCF₃ 4-349 H Cl H CF₃ CH₃ H COOH 4-350 H Cl H CF₃ CH₃ H COOCH₃ 4-351 H Cl H CF₃ CH₃ H COOC₂H₅ 4-352 H Cl H CF₃ CH₃ H COO^(n)C₃H₇ 4-353 H Cl H CF₃ CH₃ H COO^(n)C₄H₉ 4-354 H Cl H CF₃ CH₃ H COO^(n)C₅H₁₁ 4-355 H Cl H CF₃ CH₃ H COO^(i)C₃H₇ 4-356 H Cl H CF₃ CH₃ H COO^(c)C₅H₉ 4-357 H Cl H CF₃ CH₃ H COO^(c)C₆H₁₁ 4-358 H Cl H CF₃ CH₃ H COOCH₂CH═CH₂ 4-359 H Cl H CF₃ CH₃ H COOCH₂C≡CH 4-360 H Cl H CF₃ CH₃ H CONH₂ 4-361 H Cl H CF₃ CH₃ H CONHCH₃ 4-362 H Cl H CF₃ CH₃ H CONHC₂H₅ 4-363 H Cl H CF₃ CH₃ H CON(CH₃)₂ 4-364 H Cl H CF₃ CH₃ H CON(C₂H₅)₂ 4-365 F Cl H CF₃ CH₃ H CH₂Cl 4-366 F Cl H CF₃ CH₃ H CH₂Br 4-367 F Cl H CF₃ CH₃ H CH₂OCH₃ 4-368 F Cl H CF₃ CH₃ H CH₂OC₂H₅ 4-369 F Cl H CF₃ CH₃ H CH₂OCH₂OCH₃ 4-370 F Cl H CF₃ CH₃ H CH₂OCH₂OC₂H₅ 4-371 F Cl H CF₃ CH₃ H CH₂OCOCH₃ 4-372 F Cl H CF₃ CH₃ H CH₂OCOC₂H₅ 4-373 F Cl H CF₃ CH₃ H CH₂OCO^(i)C₃H₇ 4-374 F Cl H CF₃ CH₃ H CH₂OCOCH₂Cl 4-375 F Cl H CF₃ CH₃ H CH₂OCOCCl₃ 4-376 F Cl H CF₃ CH₃ H CH₂OCOCF₃ 4-377 F Cl H CF₃ CH₃ H COOH 4-378 F Cl H CF₃ CH₃ H COOCH₃ 4-379 F Cl H CF₃ CH₃ H COOC₂H₅ 4-380 F Cl H CF₃ CH₃ H COO^(n)C₃H₇ 4-381 F Cl H CF₃ CH₃ H COO^(n)C₄H₉ 4-382 F Cl H CF₃ CH₃ H COO^(n)C₅H₁₁ 4-383 F Cl H CF₃ CH₃ H COO^(i)C₃H₇ 4-384 F Cl H CF₃ CH₃ H COO^(c)C₅H₉ 4-385 F Cl H CF₃ CH₃ H COO^(c)C₆H₁₁ 4-386 F Cl H CF₃ CH₃ H COOCH₂CH═CH₂ 4-387 F Cl H CF₃ CH₃ H COOCH₂C≡CH 4-388 F Cl H CF₃ CH₃ H CONH₂ 4-389 F Cl H CF₃ CH₃ H CONHCH₃ 4-390 F Cl H CF₃ CH₃ H CONHC₂H₅ 4-391 F Cl H CF₃ CH₃ H CON(CH₃)₂ 4-392 F Cl H CF₃ CH₃ H CON(C₂H₅)₂ 4-393 H Cl H CF₃ CH₃ CH₃ CH₂Cl 4-394 H Cl H CF₃ CH₃ CH₃ CH₂Br 4-395 H Cl H CF₃ CH₃ CH₃ CH₂OCH₃ 4-396 H Cl H CF₃ CH₃ CH₃ CH₂OC₂H₅ 4-397 H Cl H CF₃ CH₃ CH₃ CH₂OCH₂OCH₃ 4-398 H Cl H CF₃ CH₃ CH₃ CH₂OCH₂OC₂H₅ 4-399 H Cl H CF₃ CH₃ CH₃ CH₂OCOCH₃ 4-400 H Cl H CF₃ CH₃ CH₃ CH₂OCOC₂H₅ 4-401 H Cl H CF₃ CH₃ CH₃ CH₂OCO^(i)C₃H₇ 4-402 H Cl H CF₃ CH₃ CH₃ CH₂OCOCH₂Cl 4-403 H Cl H CF₃ CH₃ CH₃ CH₂OCOCCl₃ 4-404 H Cl H CF₃ CH₃ CH₃ CH₂OCOCF₃ 4-405 H Cl H CF₃ CH₃ CH₃ COOH 4-406 H Cl H CF₃ CH₃ CH₃ COOCH₃ 4-407 H Cl H CF₃ CH₃ CH₃ COOC₂H₅ 4-408 H Cl H CF₃ CH₃ CH₃ COO^(n)C₃H₇ 4-409 H Cl H CF₃ CH₃ CH₃ COO^(n)C₄H₉ 4-410 H Cl H CF₃ CH₃ CH₃ COO^(n)C₅H₁₁ 4-411 H Cl H CF₃ CH₃ CH₃ COO^(i)C₃H₇ 4-412 H Cl H CF₃ CH₃ CH₃ COO^(c)C₅H₉ 4-413 H Cl H CF₃ CH₃ CH₃ COO^(c)C₆H₁₁ 4-414 H Cl H CF₃ CH₃ CH₃ COOCH₂CH═CH₂ 4-415 H Cl H CF₃ CH₃ CH₃ COOCH₂C≡CH 4-416 H Cl H CF₃ CH₃ CH₃ CONH₂ 4-417 H Cl H CF₃ CH₃ CH₃ CONHCH₃ 4-418 H Cl H CF₃ CH₃ CH₃ CONHC₂H₅ 4-419 H Cl H CF₃ CH₃ CH₃ CON(CH₃)₂ 4-420 H Cl H CF₃ CH₃ CH₃ CON(C₂H₅)₂ 4-421 F Cl H CF₃ CH₃ CH₃ CH₂Cl 4-422 F Cl H CF₃ CH₃ CH₃ CH₂Br 4-423 F Cl H CF₃ CH₃ CH₃ CH₂OCH₃ 4-424 F Cl H CF₃ CH₃ CH₃ CH₂OC₂H₅ 4-425 F Cl H CF₃ CH₃ CH₃ CH₂OCH₂OCH₃ 4-426 F Cl H CF₃ CH₃ CH₃ CH₂OCH₂OC₂H₅ 4-427 F Cl H CF₃ CH₃ CH₃ CH₂OCOCH₃ 4-428 F Cl H CF₃ CH₃ CH₃ CH₂OCOC₂H₅ 4-429 F Cl H CF₃ CH₃ CH₃ CH₂OC^(i)C₃H₇ 4-430 F Cl H CF₃ CH₃ CH₃ CH₂OCOCH₂Cl 4-431 F Cl H CF₃ CH₃ CH₃ CH₂OCOCCl₃ 4-432 F Cl H CF₃ CH₃ CH₃ CH₂OCOCF₃ 4-433 F Cl H CF₃ CH₃ CH₃ COOH 4-434 F Cl H CF₃ CH₃ CH₃ COOCH₃ 4-435 F Cl H CF₃ CH₃ CH₃ COOC₂H₅ 4-436 F Cl H CF₃ CH₃ CH₃ COO^(n)C₃H₇ 4-437 F Cl H CF₃ CH₃ CH₃ COO^(n)C₄H₉ 4-438 F Cl H CF₃ CH₃ CH₃ COO^(n)C₅H₁₁ 4-439 F Cl H CF₃ CH₃ CH₃ COO^(i)C₃H₇ 4-440 F Cl H CF₃ CH₃ CH₃ COO^(c)C₅H₉ 4-441 F Cl H CF₃ CH₃ CH₃ COO^(c)C₆H₁₁ 4-442 F Cl H CF₃ CH₃ CH₃ COOCH₂CH═CH₂ 4-443 F Cl H CF₃ CH₃ CH₃ COOCH₂C≡CH 4-444 F Cl H CF₃ CH₃ CH₃ CONH₂ 4-445 F Cl H CF₃ CH₃ CH₃ CONHCH₃ 4-446 F Cl H CF₃ CH₃ CH₃ CONHC₂H₅ 4-447 F Cl H CF₃ CH₃ CH₃ CON(CH₃)₂ 4-448 F Cl H CF₃ CH₃ CH₃ CON(C₂H₅)₂ 4-449 F Cl H CF₃ CH₃ H CH₃ 4-450 F Cl H CF₃ CH₃ H CH₂OH 4-451 F Cl H CF₃ CH₃ CH₃ CH₃ 4-452 F Cl H CF₃ CH₃ CH₃ CH₂OH 4-453 F Cl H CF₃ H H CH₃ 4-454 F Cl H CF₃ H H CH₂OH 4-455 F Cl H CF₃ H CH₃ CH₃ 4-456 F Cl H CF₃ H CH₃ CH₂OH 4-457 H Cl H CF₃ CH₃ H CH₃ 4-458 H Cl H CF₃ CH₃ H CH₂OH 4-459 H Cl H CF₃ CH₃ CH₃ CH₃ 4-460 H Cl H CF₃ CH₃ CH₃ CH₂OH 4-461 H Cl H CF₃ H H CH₃ 4-462 H Cl H CF₃ H H CH₂OH 4-463 H Cl H CF₃ H CH₃ CH₃ 4-464 H Cl H CF₃ H CH₃ CH₂OH 4-465 F Cl H CF₂Cl CH₃ H CH₃ 4-466 F Cl H CF₂Cl CH₃ H CH₂OH 4-467 F Cl H CF₂Cl CH₃ CH₃ CH₃ 4-468 F Cl H CF₂Cl CH₃ CH₃ CH₂OH 4-469 F Cl H CF₂Cl H H CH₃ 4-470 F Cl H CF₂Cl H H CH₂OH 4-471 F Cl H CF₂Cl H CH₃ CH₃ 4-472 F Cl H CF₂Cl H CH₃ CH₂OH 4-473 H Cl H CF₂Cl CH₃ H CH₃ 4-474 H Cl H CF₂Cl CH₃ H CH₂OH 4-475 H Cl H CF₂Cl CH₃ CH₃ CH₃ 4-476 H Cl H CF₂Cl CH₃ CH₃ CH₂OH 4-477 H Cl H CF₂Cl H H CH₃ 4-478 H Cl H CF₂Cl H H CH₂OH 4-479 H Cl H CF₂Cl H CH₃ CH₃ 4-480 H Cl H CF₂Cl H CH₃ CH₂OH 4-481 H Cl H CF₃ H H CH₂Cl 4-482 H Cl H CF₃ H H CH₂Br 4-483 H Cl H CF₃ H H CH₂OCH₃ 4-484 H Cl H CF₃ H H CH₂OC₂H₅ 4-485 H Cl H CF₃ H H CH₂OCH₂OCH₃ 4-486 H Cl H CF₃ H H CH₂OCH₂OC₂H₅ 4-487 H Cl H CF₃ H H CH₂OCOCH₃ 4-488 H Cl H CF₃ H H CH₂OCOC₂H₅ 4-489 H Cl H CF₃ H H CH₂OCO^(i)C₃H₇ 4-490 H Cl H CF₃ H H CH₂OCOCH₂Cl 4-491 H Cl H CF₃ H H CH₂OCOCCl₃ 4-492 H Cl H CF₃ H H CH₂OCOCF₃ 4-493 H Cl H CF₃ H H COOH 4-494 H Cl H CF₃ H H COOCH₃ 4-495 H Cl H CF₃ H H COOC₂H₅ 4-496 H Cl H CF₃ H H COO^(n)C₃H₇ 4-497 H Cl H CF₃ H H COO^(n)C₄H₉ 4-498 H Cl H CF₃ H H COO^(n)C₅H₁₁ 4-499 H Cl H CF₃ H H COO^(i)C₃H₇ 4-500 H Cl H CF₃ H H COO^(c)C₅H₉ 4-501 H Cl H CF₃ H H COO^(c)C₆H₁₁ 4-502 H Cl H CF₃ H H COOCH₂CH═CH₂ 4-503 H Cl H CF₃ H H COOCH₂C≡CH 4-504 H Cl H CF₃ H H CONH₂ 4-505 H Cl H CF₃ H H CONHCH₃ 4-506 H Cl H CF₃ H H CONHC₂H₅ 4-507 H Cl H CF₃ H H CON(CH₃)₂ 4-508 H Cl H CF₃ H H CON(C₂H₅)₂ 4-509 F Cl H CF₃ H H CH₂Cl 4-510 F Cl H CF₃ H H CH₂Br 4-511 F Cl H CF₃ H H CH₂OCH₃ 4-512 F Cl H CF₃ H H CH₂OC₂H₅ 4-513 F Cl H CF₃ H H CH₂OCH₂OCH₃ 4-514 F Cl H CF₃ H H CH₂OCH₂OC₂H₅ 4-515 F Cl H CF₃ H H CH₂OCOCH₃ 4-516 F Cl H CF₃ H H CH₂OCOC₂H₅ 4-517 F Cl H CF₃ H H CH₂OCO^(i)C₃H₇ 4-518 F Cl H CF₃ H H CH₂OCOCH₂Cl 4-519 F Cl H CF₃ H H CH₂OCOCCl₃ 4-520 F Cl H CF₃ H H CH₂OCOCF₃ 4-521 F Cl H CF₃ H H COOH 4-522 F Cl H CF₃ H H COOCH₃ 4-523 F Cl H CF₃ H H COOC₂H₅ 4-524 F Cl H CF₃ H H COO^(n)C₃H₇ 4-525 F Cl H CF₃ H H COO^(n)C₄H₉ 4-526 F Cl H CF₃ H H COO^(n)C₅H₁₁ 4-527 F Cl H CF₃ H H COO^(i)C₃H₇ 4-528 F Cl H CF₃ H H COO^(c)C₅H₉ 4-529 F Cl H CF₃ H H COO^(c)C₆H₁₁ 4-530 F Cl H CF₃ H H COOCH₂CH═CH₂ 4-531 F Cl H CF₃ H H COOCH₂C≡CH 4-532 F Cl H CF₃ H H CONH₂ 4-533 F Cl H CF₃ H H CONHCH₃ 4-534 F Cl H CF₃ H H CONHC₂H₅ 4-535 F Cl H CF₃ H H CON(CH₃)₂ 4-536 F Cl H CF₃ H H CON(C₂H₅)₂ 4-537 H Cl H CF₃ H CH₃ CH₂Cl 4-538 H Cl H CF₃ H CH₃ CH₂Br 4-539 H Cl H CF₃ H CH₃ CH₂OCH₃ 4-540 H Cl H CF₃ H CH₃ CH₂OC₂H₅ 4-541 H Cl H CF₃ H CH₃ CH₂OCH₂OCH₃ 4-542 H Cl H CF₃ H CH₃ CH₂OCH₂OC₂H₅ 4-543 H Cl H CF₃ H CH₃ CH₂OCOCH₃ 4-544 H Cl H CF₃ H CH₃ CH₂OCOC₂H₅ 4-545 H Cl H CF₃ H CH₃ CH₂OCO^(i)C₃H₇ 4-546 H Cl H CF₃ H CH₃ CH₂OCOCH₂Cl 4-547 H Cl H CF₃ H CH₃ CH₂OCOCCl₃ 4-548 H Cl H CF₃ H CH₃ CH₂OCOCF₃ 4-549 H Cl H CF₃ H CH₃ COOH 4-550 H Cl H CF₃ H CH₃ COOCH₃ 4-551 H Cl H CF₃ H CH₃ COOC₂H₅ 4-552 H Cl H CF₃ H CH₃ COO^(n)C₃H₇ 4-553 H Cl H CF₃ H CH₃ COO^(n)C₄H₉ 4-554 H Cl H CF₃ H CH₃ COO^(n)C₅H₁₁ 4-555 H Cl H CF₃ H CH₃ COO^(i)C₃H₇ 4-556 H Cl H CF₃ H CH₃ COO^(c)C₅H₉ 4-557 H Cl H CF₃ H CH₃ COO^(c)C₆H₁₁ 4-558 H Cl H CF₃ H CH₃ COOCH₂CH═CH₂ 4-559 H Cl H CF₃ H CH₃ COOCH₂C≡CH 4-560 H Cl H CF₃ H CH₃ CONH₂ 4-561 H Cl H CF₃ H CH₃ CONHCH₃ 4-562 H Cl H CF₃ H CH₃ CONHC₂H₅ 4-563 H Cl H CF₃ H CH₃ CON(CH₃)₂ 4-564 H Cl H CF₃ H CH₃ CON(C₂H₅)₂ 4-565 F Cl H CF₃ H CH₃ CH₂Cl 4-566 F Cl H CF₃ H CH₃ CH₂Br 4-567 F Cl H CF₃ H CH₃ CH₂OCH₃ 4-568 F Cl H CF₃ H CH₃ CH₂OC₂H₅ 4-569 F Cl H CF₃ H CH₃ CH₂OCH₂OCH₃ 4-570 F Cl H CF₃ H CH₃ CH₂OCH₂OC₂H₅ 4-571 F Cl H CF₃ H CH₃ CH₂OCOCH₃ 4-572 F Cl H CF₃ H CH₃ CH₂OCOC₂H₅ 4-573 F Cl H CF₃ H CH₃ CH₂OCO^(i)C₃H₇ 4-574 F Cl H CF₃ H CH₃ CH₂OCOCH₂Cl 4-575 F Cl H CF₃ H CH₃ CH₂OCOCCl₃ 4-576 F Cl H CF₃ H CH₃ CH₂OCOCF₃ 4-577 F Cl H CF₃ H CH₃ COOH 4-578 F Cl H CF₃ H CH₃ COOCH₃ 4-579 F Cl H CF₃ H CH₃ COOC₂H₅ 4-580 F Cl H CF₃ H CH₃ COO^(n)C₃H₇ 4-581 F Cl H CF₃ H CH₃ COO^(n)C₄H₉ 4-582 F Cl H CF₃ H CH₃ COO^(n)C₅H₁₁ 4-583 F Cl H CF₃ H CH₃ COO^(i)C₃H₇ 4-584 F Cl H CF₃ H CH₃ COO^(c)C₅H₉ 4-585 F Cl H CF₃ H CH₃ COO^(c)C₆H₁₁ 4-586 F Cl H CF₃ H CH₃ COOCH₂CH═CH₂ 4-587 F Cl H CF₃ H CH₃ COOCH₂C≡CH 4-588 F Cl H CF₃ H CH₃ CONH₂ 4-589 F Cl H CF₃ H CH₃ CONHCH₃ 4-590 F Cl H CF₃ H CH₃ CONHC₂H₅ 4-591 F Cl H CF₃ H CH₃ CON(CH₃)₂ 4-592 F Cl H CF₃ H CH₃ CON(C₂H₅)₂ 4-593 H Cl H CF₃ H H CH₂Cl 4-594 H Cl H CF₃ H H CH₂Br 4-595 H Cl H CF₃ H H CH₂OCH₃ 4-596 H Cl H CF₃ H H CH₂OC₂H₅ 4-597 H Cl H CF₃ H H CH₂OCH₂OCH₃ 4-598 H Cl H CF₃ H H CH₂OCH₂OC₂H₅ 4-599 H Cl H CF₃ H H CH₂OCOCH₃ 4-600 H Cl H CF₃ H H CH₂OCOC₂H₅ 4-601 H Cl H CF₃ H H CH₂OCO^(i)C₃H₇ 4-602 H Cl H CF₃ H H CH₂OCOCH₂Cl 4-603 H Cl H CF₃ H H CH₂OCOCCl₃ 4-604 H Cl H CF₃ H H CH₂OCOCF₃ 4-605 H Cl H CF₃ H H COOH 4-606 H Cl H CF₃ H H COOCH₃ 4-607 H Cl H CF₃ H H COOC₂H₅ 4-608 H Cl H CF₃ H H COO^(n)C₃H₇ 4-609 H Cl H CF₃ H H COO^(n)C₄H₉ 4-610 H Cl H CF₃ H H COO^(n)C₅H₁₁ 4-611 H Cl H CF₃ H H COO^(i)C₃H₇ 4-612 H Cl H CF₃ H H COO^(c)C₅H₉ 4-613 H Cl H CF₃ H H COO^(c)C₆H₁₁ 4-614 H Cl H CF₃ H H COOCH₂CH═CH₂ 4-615 H Cl H CF₃ H H COOCH₂C≡CH 4-616 H Cl H CF₃ H H CONH₂ 4-617 H Cl H CF₃ H H CONHCH₃ 4-618 H Cl H CF₃ H H CONHC₂H₅ 4-619 H Cl H CF₃ H H CON(CH₃)₂ 4-620 H Cl H CF₃ H H CON(C₂H₅)₂ 4-621 F Cl H CF₃ H H CH₂Cl 4-622 F Cl H CF₃ H H CH₂Br 4-623 F Cl H CF₃ H H CH₂OCH₃ 4-624 F Cl H CF₃ H H CH₂OC₂H₅ 4-625 F Cl H CF₃ H H CH₂OCH₂OCH₃ 4-626 F Cl H CF₃ H H CH₂OCH₂OC₂H₅ 4-627 F Cl H CF₃ H H CH₂OCOCH₃ 4-628 F Cl H CF₃ H H CH₂OCOC₂H₅ 4-629 F Cl H CF₃ H H CH₂OCO^(i)C₃H₇ 4-630 F Cl H CF₃ H H CH₂OCOCH₂Cl 4-631 F Cl H CF₃ H H CH₂OCOCCl₃ 4-632 F Cl H CF₃ H H CH₂OCOCF₃ 4-633 F Cl H CF₃ H H COOH 4-634 F Cl H CF₃ H H COOCH₃ 4-635 F Cl H CF₃ H H COOC₂H₅ 4-636 F Cl H CF₃ H H COO^(n)C₃H₇ 4-637 F Cl H CF₃ H H COO^(n)C₄H₉ 4-638 F Cl H CF₃ H H COO^(n)C₅H₁₁ 4-639 F Cl H CF₃ H H COO^(i)C₃H₇ 4-640 F Cl H CF₃ H H COO^(c)C₅H₉ 4-641 F Cl H CF₃ H H COO^(c)C₆H₁₁ 4-642 F Cl H CF₃ H H COOCH₂CH═CH₂ 4-643 F Cl H CF₃ H H COOCH₂C≡CH 4-644 F Cl H CF₃ H H CONH₂ 4-645 F Cl H CF₃ H H CONHCH₃ 4-646 F Cl H CF₃ H H CONHC₂H₅ 4-647 F Cl H CF₃ H H CON(CH₃)₂ 4-648 F Cl H CF₃ H H CON(C₂H₅)₂ 4-649 H Cl H CF₃ H CH₃ CH₂Cl 4-650 H Cl H CF₃ H CH₃ CH₂Br 4-651 H Cl H CF₃ H CH₃ CH₂OCH₃ 4-652 H Cl H CF₃ H CH₃ CH₂OC₂H₅ 4-653 H Cl H CF₃ H CH₃ CH₂OCH₂OCH₃ 4-654 H Cl H CF₃ H CH₃ CH₂OCH₂OC₂H₅ 4-655 H Cl H CF₃ H CH₃ CH₂OCOCH₃ 4-656 H Cl H CF₃ H CH₃ CH₂OCOC₂H₅ 4-657 H Cl H CF₃ H CH₃ CH₂OCO^(i)C₃H₇ 4-658 H Cl H CF₃ H CH₃ CH₂OCOCH₂Cl 4-659 H Cl H CF₃ H CH₃ CH₂OCOCCl₃ 4-660 H Cl H CF₃ H CH₃ CH₂OCOCF₃ 4-661 H Cl H CF₃ H CH₃ COOH 4-662 H Cl H CF₃ H CH₃ COOCH₃ 4-663 H Cl H CF₃ H CH₃ COOC₂H₅ 4-664 H Cl H CF₃ H CH₃ COO^(n)C₃H₇ 4-665 H Cl H CF₃ H CH₃ COO^(n)C₄H₉ 4-666 H Cl H CF₃ H CH₃ COO^(n)C₅H₁₁ 4-667 H Cl H CF₃ H CH₃ COO^(i)C₃H₇ 4-668 H Cl H CF₃ H CH₃ COO^(c)C₅H₉ 4-669 H Cl H CF₃ H CH₃ COO^(c)C₆H₁₁ 4-670 H Cl H CF₃ H CH₃ COOCH₂CH═CH₂ 4-671 H Cl H CF₃ H CH₃ COOCH₂C≡CH 4-672 H Cl H CF₃ H CH₃ CONH₂ 4-673 H Cl H CF₃ H CH₃ CONHCH₃ 4-674 H Cl H CF₃ H CH₃ CONHC₂H₅ 4-675 H Cl H CF₃ H CH₃ CON(CH₃)₂ 4-676 H Cl H CF₃ H CH₃ CON(C₂H₅)₂ 4-677 F Cl H CF₃ H CH₃ CH₂Cl 4-678 F Cl H CF₃ H CH₃ CH₂Br 4-679 F Cl H CF₃ H CH₃ CH₂OCH₃ 4-680 F Cl H CF₃ H CH₃ CH₂OC₂H₅ 4-681 F Cl H CF₃ H CH₃ CH₂OCH₂OCH₃ 4-682 F Cl H CF₃ H CH₃ CH₂OCH₂OC₂H₅ 4-683 F Cl H CF₃ H CH₃ CH₂OCOCH₃ 4-684 F Cl H CF₃ H CH₃ CH₂OCOC₂H₅ 4-685 F Cl H CF₃ H CH₃ CH₂OCO^(i)C₃H₇ 4-686 F Cl H CF₃ H CH₃ CH₂OCOCH₂Cl 4-687 F Cl H CF₃ H CH₃ CH₂OCOCCl₃ 4-688 F Cl H CF₃ H CH₃ CH₂OCOCF₃ 4-689 F Cl H CF₃ H CH₃ COOH 4-690 F Cl H CF₃ H CH₃ COOCH₃ 4-691 F Cl H CF₃ H CH₃ COOC₂H₅ 4-692 F Cl H CF₃ H CH₃ COO^(n)C₃H₇ 4-693 F Cl H CF₃ H CH₃ COO^(n)C₄H₉ 4-694 F Cl H CF₃ H CH₃ COO^(n)C₅H₁₁ 4-695 F Cl H CF₃ H CH₃ COO^(i)C₃H₇ 4-696 F Cl H CF₃ H CH₃ COO^(c)C₅H₉ 4-697 F Cl H CF₃ H CH₃ COO^(c)C₅H₁₁ 4-698 F Cl H CF₃ H CH₃ COOCH₂CH═CH₂ 4-699 F Cl H CF₃ H CH₃ COOCH₂C≡CH 4-700 F Cl H CF₃ H CH₃ CONH₂ 4-701 F Cl H CF₃ H CH₃ CONHCH₃ 4-702 F Cl H CF₃ H CH₃ CONHC₂H₅ 4-703 F Cl H CF₃ H CH₃ CON(CH₃)₂ 4-704 F Cl H CF₃ H CH₃ CON(C₂H₅)₂ 4-705 H Cl CH₃ CF₃ H H CH₂Cl 4-706 H Cl CH₃ CF₃ H H CH₂Br 4-707 H Cl CH₃ CF₃ H H CH₂OCH₃ 4-708 H Cl CH₃ CF₃ H H CH₂OC₂H₅ 4-709 H Cl CH₃ CF₃ H H CH₂OCH₂OCH₃ 4-710 H Cl CH₃ CF₃ H H CH₂OCH₂OC₂H₅ 4-711 H Cl CH₃ CF₃ H H CH₂OCOCH₃ 4-712 H Cl CH₃ CF₃ H H CH₂OCOC₂H₅ 4-713 H Cl CH₃ CF₃ H H CH₂OCO^(i)C₃H₇ 4-714 H Cl CH₃ CF₃ H H CH₂OCOCH₂Cl 4-715 H Cl CH₃ CF₃ H H CH₂OCOCCl₃ 4-716 H Cl CH₃ CF₃ H H CH₂OCOCF₃ 4-717 H Cl CH₃ CF₃ H H COOH 4-718 H Cl CH₃ CF₃ H H COOCH₃ 4-719 H Cl CH₃ CF₃ H H COOC₂H₅ 4-720 H Cl CH₃ CF₃ H H COO^(n)C₃H₇ 4-721 H Cl CH₃ CF₃ H H COO^(n)C₄H₉ 4-722 H Cl CH₃ CF₃ H H COO^(n)C₅H₁₁ 4-723 H Cl CH₃ CF₃ H H COO^(i)C₃H₇ 4-724 H Cl CH₃ CF₃ H H COO^(c)C₅H₉ 4-725 H Cl CH₃ CF₃ H H COO^(c)C₆H₁₁ 4-726 H Cl CH₃ CF₃ H H COOCH₂CH═CH₂ 4-727 H Cl CH₃ CF₃ H H COOCH₂C≡CH 4-728 H Cl CH₃ CF₃ H H CONH₂ 4-729 H Cl CH₃ CF₃ H H CONHCH₃ 4-730 H Cl CH₃ CF₃ H H CONHC₂H₅ 4-731 H Cl CH₃ CF₃ H H CON(CH₃)₂ 4-732 H Cl CH₃ CF₃ H H CON(C₂H₅)₂ 4-733 F Cl CH₃ CF₃ H H CH₂Cl 4-734 F Cl CH₃ CF₃ H H CH₂Br 4-735 F Cl CH₃ CF₃ H H CH₂OCH₃ 4-736 F Cl CH₃ CF₃ H H CH₂OC₂H₅ 4-737 F Cl CH₃ CF₃ H H CH₂OCH₂OCH₃ 4-738 F Cl CH₃ CF₃ H H CH₂OCH₂OC₂H₅ 4-739 F Cl CH₃ CF₃ H H CH₂OCOCH₃ 4-740 F Cl CH₃ CF₃ H H CH₂OCOC₂H₅ 4-741 F Cl CH₃ CF₃ H H CH₂OCO^(i)C₃H₇ 4-742 F Cl CH₃ CF₃ H H CH₂OCOCH₂Cl 4-743 F Cl CH₃ CF₃ H H CH₂OCOCCl₃ 4-744 F Cl CH₃ CF₃ H H CH₂OCOCF₃ 4-745 F Cl CH₃ CF₃ H H COOH 4-746 F Cl CH₃ CF₃ H H COOCH₃ 4-747 F Cl CH₃ CF₃ H H COOC₂H₅ 4-748 F Cl CH₃ CF₃ H H COO^(n)C₃H₇ 4-749 F Cl CH₃ CF₃ H H COO^(n)C₄H₉ 4-750 F Cl CH₃ CF₃ H H COO^(n)C₅H₁₁ 4-751 F Cl CH₃ CF₃ H H COO^(i)C₃H₇ 4-752 F Cl CH₃ CF₃ H H COO^(c)C₅H₉ 4-753 F Cl CH₃ CF₃ H H COO^(c)C₆H₁₁ 4-754 F Cl CH₃ CF₃ H H COOCH₂CH═CH₂ 4-755 F Cl CH₃ CF₃ H H COOCH₂C≡CH 4-75& F Cl CH₃ CF₃ H H CONH₂ 4-757 F Cl CH₃ CF₃ H H CONHCH₃ 4-758 F Cl CH₃ CF₃ H H CONHC₂H₅ 4-759 F Cl CH₃ CF₃ H H CON(CH₃)₂ 4-760 F Cl CH₃ CF₃ H H CON(C₂H₅)₂ 4-761 H Cl CH₃ CF₃ H CH₃ CH₂Cl 4-762 H Cl CH₃ CF₃ H CH₃ CH₂Br 4-763 H Cl CH₃ CF₃ H CH₃ CH₂OCH₃ 4-764 H Cl CH₃ CF₃ H CH₃ CH₂OC₂H₅ 4-765 H Cl CH₃ CF₃ H CH₃ CH₂OCH₂OCH₃ 4-766 H Cl CH₃ CF₃ H CH₃ CH₂OCH₂OC₂H₅ 4-767 H Cl CH₃ CF₃ H CH₃ CH₂OCOCH₃ 4-768 H Cl CH₃ CF₃ H CH₃ CH₂OCOC₂H₅ 4-769 H Cl CH₃ CF₃ H CH₃ CH₂OCO^(i)C₃H₇ 4-770 H Cl CH₃ CF₃ H CH₃ CH₂OCOCH₂Cl 4-771 H Cl CH₃ CF₃ H CH₃ CH₂OCOCCl₃ 4-772 H Cl CH₃ CF₃ H CH₃ CH₂OCOCF₃ 4-773 H Cl CH₃ CF₃ H CH₃ COOH 4-774 H Cl CH₃ CF₃ H CH₃ COOCH₃ 4-775 H Cl CH₃ CF₃ H CH₃ COOC₂H₅ 4-776 H Cl CH₃ CF₃ H CH₃ COO^(n)C₃H₇ 4-777 H Cl CH₃ CF₃ H CH₃ COO^(n)C₄H₉ 4-778 H Cl CH₃ CF₃ H CH₃ COO^(n)C₅H₁₁ 4-779 H Cl CH₃ CF₃ H CH₃ COO^(i)C₃H₇ 4-780 H Cl CH₃ CF₃ H CH₃ COO^(c)C₅H₉ 4-781 H Cl CH₃ CF₃ H CH₃ COO^(c)C₆H₁₁ 4-782 H Cl CH₃ CF₃ H CH₃ COOCH₂CH═CH₂ 4-783 H Cl CH₃ CF₃ H CH₃ COOCH₂C≡CH 4-784 H Cl CH₃ CF₃ H CH₃ CONH₂ 4-785 H Cl CH₃ CF₃ H CH₃ CONHCH₃ 4-786 H Cl CH₃ CF₃ H CH₃ CONHC₂H₅ 4-787 H Cl CH₃ CF₃ H CH₃ CON(CH₃)₂ 4-788 H Cl CH₃ CF₃ H CH₃ CON(C₂H₅)₂ 4-789 F Cl CH₃ CF₃ H CH₃ CH₂Cl 4-790 F Cl CH₃ CF₃ H CH₃ CH₂Br 4-791 F Cl CH₃ CF₃ H CH₃ CH₂OCH 4-792 F Cl CH₃ CF₃ H CH₃ CH₂OC₂H₅ 4-793 F Cl CH₃ CF₃ H CH₃ CH₂OCH₂OCH₃ 4-794 F Cl CH₃ CF₃ H CH₃ CH₂OCH₂OC₂H₅ 4-795 F Cl CH₃ CF₃ H CH₃ CH₂OCOCH₃ 4-796 F Cl CH₃ CF₃ H CH₃ CH₂OCOC₂H₅ 4-797 F Cl CH₃ CF₃ H CH₃ CH₂OCO^(i)C₃H₇ 4-798 F Cl CH₃ CF₃ H CH₃ CH₂OCOCH₂Cl 4-799 F Cl CH₃ CF₃ H CH₃ CH₂OCOCCl₃ 4-800 F Cl CH₃ CF₃ H CH₃ CH₂OCOCF₃ 4-801 F Cl CH₃ CF₃ H CH₃ COOH 4-802 F Cl CH₃ CF₃ H CH₃ COOCH₃ 4-803 F Cl CH₃ CF₃ H CH₃ COOC₂H₅ 4-804 F Cl CH₃ CF₃ H CH₃ COO^(n)C₃H₇ 4-805 F Cl CH₃ CF₃ H CH₃ COO^(n)C₄H₉ 4-806 F Cl CH₃ CF₃ H CH₃ COO^(n)C₅H₁₁ 4-807 F Cl CH₃ CF₃ H CH₃ COO^(i)C₃H₇ 4-808 F Cl CH₃ CF₃ H CH₃ COO^(c)C₅H₉ 4-809 F Cl CH₃ CF₃ H CH₃ COO^(c)C₆H₁₁ 4-810 F Cl CH₃ CF₃ H CH₃ COOCH₂CH═CH₂ 4-811 F Cl CH₃ CF₃ H CH₃ COOCH₂C≡CH 4-812 F Cl CH₃ CF₃ H CH₃ CONH₂ 4-813 F Cl CH₃ CF₃ H CH₃ CONHCH₃ 4-814 F Cl CH₃ CF₃ H CH₃ CONHC₂H₅ 4-815 F Cl CH₃ CF₃ H CH₃ CON(CH₃)₂ 4-816 F Cl CH₃ CF₃ H CH₃ CON(C₂H₅)₂ 4-817 H Cl CH₃ CF₃ H H CH₂Cl 4-818 H Cl CH₃ CF₃ H H CH₂Br 4-819 H Cl CH₃ CF₃ H H CH₂OCH₃ 4-820 H Cl CH₃ CF₃ H H CH₂OC₂H₅ 4-821 H Cl CH₃ CF₃ H H CH₂OCH₂OCH₃ 4-822 H Cl CH₃ CF₃ H H CH₂OCH₂OC₂H₅ 4-823 H Cl CH₃ CF₃ H H CH₂OCOCH₃ 4-824 H Cl CH₃ CF₃ H H CH₂OCOC₂H₅ 4-825 H Cl CH₃ CF₃ H H CH₂OCO^(i)C₃H₇ 4-826 H Cl CH₃ CF₃ H H CH₂OCOCH₂Cl 4-827 H Cl CH₃ CF₃ H H CH₂OCOCCl₃ 4-828 H Cl CH₃ CF₃ H H CH₂OCOCF₃ 4-829 H Cl CH₃ CF₃ H H COOH 4-830 H Cl CH₃ CF₃ H H COOCH₃ 4-831 H Cl CH₃ CF₃ H H COOC₂H₅ 4-832 H Cl CH₃ CF₃ H H COO^(n)C₃H₇ 4-833 H Cl CH₃ CF₃ H H COO^(n)C₄H₉ 4-834 H Cl CH₃ CF₃ H H COO^(n)C₅H₁₁ 4-835 H Cl CH₃ CF₃ H H COO^(i)C₃H₇ 4-836 H Cl CH₃ CF₃ H H COO^(c)C₅H₉ 4-837 H Cl CH₃ CF₃ H H COO^(c)C₆H₁₁ 4-838 H Cl CH₃ CF₃ H H COOCH₂CH═CH₂ 4-839 H Cl CH₃ CF₃ H H COOCH₂C≡CH 4-840 H Cl CH₃ CF₃ H H CONH₂ 4-841 H Cl CH₃ CF₃ H H CONHCH₃ 4-842 H Cl CH₃ CF₃ H H CONHC₂H₅ 4-843 H Cl CH₃ CF₃ H H CON(CH₃)₂ 4-844 H Cl CH₃ CF₃ H H CON(C₂H₅)₂ 4-845 F Cl CH₃ CF₃ H H CH₂Cl 4-846 F Cl CH₃ CF₃ H H CH₂Br 4-847 F Cl CH₃ CF₃ H H CH₂OCH₃ 4-848 F Cl CH₃ CF₃ H H CH₂OC₂H₅ 4-849 F Cl CH₃ CF₃ H H CH₂OCH₂OCH₃ 4-850 F Cl CH₃ CF₃ H H CH₂OCH₂OC₂H₅ 4-851 F Cl CH₃ CF₃ H H CH₂OCOCH₃ 4-852 F Cl CH₃ CF₃ H H CH₂OCOC₂H₅ 4-853 F Cl CH₃ CF₃ H H CH₂OCO^(i)C₃H₇ 4-854 F Cl CH₃ CF₃ H H CH₂OCOCH₂Cl 4-855 F Cl CH₃ CF₃ H H CH₂OCOCCl₃ 4-856 F Cl CH₃ CF₃ H H CH₂OCOCF₃ 4-857 F Cl CH₃ CF₃ H H COOH 4-858 F Cl CH₃ CF₃ H H COOCH₃ 4-859 F Cl CH₃ CF₃ H H COOC₂H₅ 4-860 F Cl CH₃ CF₃ H H COO^(n)C₃H₇ 4-861 F Cl CH₃ CF₃ H H COO^(n)C₄H₉ 4-862 F Cl CH₃ CF₃ H H COO^(n)C₅H₁₁ 4-863 F Cl CH₃ CF₃ H H COO^(i)C₃H₇ 4-864 F Cl CH₃ CF₃ H H COO^(c)C₅H₉ 4-865 F Cl CH₃ CF₃ H H COO^(c)C₆H₁₁ 4-866 F Cl CH₃ CF₃ H H COOCH₂CH═CH₂ 4-867 F Cl CH₃ CF₃ H H COOCH₂C≡CH 4-868 F Cl CH₃ CF₃ H H CONH₂ 4-869 F Cl CH₃ CF₃ H H CONHCH₃ 4-870 F Cl CH₃ CF₃ H H CONHC₂H₅ 4-871 F Cl CH₃ CF₃ H H CON(CH₃)₂ 4-872 F Cl CH₃ CF₃ H H CON(C₂H₅)₂ 4-873 H Cl CH₃ CF₃ H CH₃ CH₂Cl 4-874 H Cl CH₃ CF₃ H CH₃ CH₂Br 4-875 H Cl CH₃ CF₃ H CH₃ CH₂OCH₃ 4-876 H Cl CH₃ CF₃ H CH₃ CH₂OC₂H₅ 4-877 H Cl CH₃ CF₃ H CH₃ CH₂OCH₂OCH₃ 4-878 H Cl CH₃ CF₃ H CH₃ CH₂OCH₂OC₂H₅ 4-879 H Cl CH₃ CF₃ H CH₃ CH₂OCOCH₃ 4-880 H Cl CH₃ CF₃ H CH₃ CH₂OCOC₂H₅ 4-881 H Cl CH₃ CF₃ H CH₃ CH₂OCO^(i)C₃H₇ 4-882 H Cl CH₃ CF₃ H CH₃ CH₂OCOCH₂Cl 4-883 H Cl CH₃ CF₃ H CH₃ CH₂OCOCCl₃ 4-884 H Cl CH₃ CF₃ H CH₃ CH₂OCOCF₃ 4-885 H Cl CH₃ CF₃ H CH₃ COOH 4-886 H Cl CH₃ CF₃ H CH₃ COOCH₃ 4-887 H Cl CH₃ CF₃ H CH₃ COOC₂H₅ 4-888 H Cl CH₃ CF₃ H CH₃ COO^(n)C₃H₇ 4-889 H Cl CH₃ CF₃ H CH₃ COO^(n)C₄H₉ 4-890 H Cl CH₃ CF₃ H CH₃ COO^(n)C₅H₁₁ 4-891 H Cl CH₃ CF₃ H CH₃ COO^(i)C₃H₇ 4-892 H Cl CH₃ CF₃ H CH₃ COO^(c)C₅H₉ 4-893 H Cl CH₃ CF₃ H CH₃ COO^(c)C₆H₁₁ 4-894 H Cl CH₃ CF₃ H CH₃ COOCH₂CH═CH₂ 4-895 H Cl CH₃ CF₃ H CH₃ COOCH₂C≡CH 4-896 H Cl CH₃ CF₃ H CH₃ CONH₂ 4-897 H Cl CH₃ CF₃ H CH₃ CONHCH₃ 4-898 H Cl CH₃ CF₃ H CH₃ CONHC₂H₅ 4-899 H Cl CH₃ CF₃ H CH₃ CON(CH₃)₂ 4-900 H Cl CH₃ CF₃ H CH₃ CON(C₂H₅)₂ 4-901 F Cl CH₃ CF₃ H CH₃ CH₂Cl 4-902 F Cl CH₃ CF₃ H CH₃ CH₂Br 4-903 F Cl CH₃ CF₃ H CH₃ CH₂OCH₃ 4-904 F Cl CH₃ CF₃ H CH₃ CH₂OC₂H₅ 4-905 F Cl CH₃ CF₃ H CH₃ CH₂OCH₂OCH₃ 4-906 F Cl CH₃ CF₃ H CH₃ CH₂OCH₂OC₂H₅ 4-907 F Cl CH₃ CF₃ H CH₃ CH₂OCOCH₃ 4-908 F Cl CH₃ CF₃ H CH₃ CH₂OCOC₂H₅ 4-909 F Cl CH₃ CF₃ H CH₃ CH₂OCO^(i)C₃H₇ 4-910 F Cl CH₃ CF₃ H CH₃ CH₂OCOCH₂Cl 4-911 F Cl CH₃ CF₃ H CH₃ CH₂OCOCCl₃ 4-912 F Cl CH₃ CF₃ H CH₃ CH₂OCOCF₃ 4-913 F Cl CH₃ CF₃ H CH₃ COOH 4-914 F Cl CH₃ CF₃ H CH₃ COOCH₃ 4-915 F Cl CH₃ CF₃ H CH₃ COOC₂H₅ 4-916 F Cl CH₃ CF₃ H CH₃ COO^(n)C₃H₇ 4-917 F Cl CH₃ CF₃ H CH₃ COO^(n)C₄H₉ 4-918 F Cl CH₃ CF₃ H CH₃ COO^(n)C₅H₁₁ 4-919 F Cl CH₃ CF₃ H CH₃ COO^(i)C₃H₇ 4-920 F Cl CH₃ CF₃ H CH₃ COO^(c)C₅H₉ 4-921 F Cl CH₃ CF₃ H CH₃ COO^(c)C₆H₁₁ 4-922 F Cl CH₃ CF₃ H CH₃ COOCH₂CH═CH₂ 4-923 F Cl CH₃ CF₃ H CH₃ COOCH₂C≡CH 4-924 F Cl CH₃ CF₃ H CH₃ CONH₂ 4-925 F Cl CH₃ CF₃ H CH₃ CONHCH₃ 4-926 F Cl CH₃ CF₃ H CH₃ CONHC₂H₅ 4-927 F Cl CH₃ CF₃ H CH₃ CON(CH₃)₂ 4-928 F Cl CH₃ CF₃ H CH₃ CON(C₂H₅)₂ 4-929 F Cl CH₃ CF₃ H H CH₃ 4-930 F Cl CH₃ CF₃ H H CH₂OH 4-931 F Cl CH₃ CF₃ H CH₃ CH₃ 4-932 F Cl CH₃ CF₃ H CH₃ CH₂OH 4-933 H Cl CH₃ CF₃ H H CH₃ 4-934 H Cl CH₃ CF₃ H H CH₂OH 4-935 H Cl CH₃ CF₃ H CH₃ CH₃ 4-936 H Cl CH₃ CF₃ H CH₃ CH₂OH

TABLE 5 Compounds of the formula:

Compound No. X R³ R¹ R² R⁵ 5-1  H H CF₂Cl CH₃ CH₃ 5-2  H H CF₂Cl CH₃ C₂H₅ 5-3  H H CF₂Cl CH₃ ^(i)C₃H₇ 5-4  H H CF₂Cl CH₃ ^(n)C₃H₇ 5-5  H H CF₂Cl CH₃ ^(i)C₄H₉ 5-6  H H CF₂Cl CH₃ CH₂CH═CH₂ 5-7  H H CF₂Cl CH₃ CH(CH₃)CH═CH₂ 5-8  H H CF₂Cl CH₃ CH₂C≡CH 5-9  H H CF₂Cl CH₃ CH(CH₃)C≡CH 5-10 F H CF₂Cl CH₃ CH₃ 5-11 F H CF₂Cl CH₃ C₂H₅ 5-12 F H CF₂Cl CH₃ ^(i)C₃H₇ 5-13 F H CF₂Cl CH₃ ^(n)C₃H₇ 5-14 F H CF₂Cl CH₃ ^(i)C₄H₉ 5-15 F H CF₂Cl CH₃ CH₂CH═CH₂ 5-16 F H CF₂Cl CH₃ CH(CH₃)CH═CH₂ 5-17 F H CF₂Cl CH₃ CH₂C≡CH 5-18 F H CF₂Cl CH₃ CH(CH₃)C≡CH 5-19 H H CF₃ CH₃ CH₃ 5-20 H H CF₃ CH₃ C₂H₅ 5-21 H H CF₃ CH₃ ^(i)C₃H₇ 5-22 H H CF₃ CH₃ ^(n)C₃H₇ 5-23 H H CF₃ CH₃ ^(i)C₄H₉ 5-24 H H CF₃ CH₃ CH₂CH═CH₂ 5-25 H H CF₃ CH₃ CH(CH₃)CH═CH₂ 5-26 H H CF₃ CH₃ CH₂C≡CH 5-27 H H CF₃ CH₃ CH(CH₃)C≡CH 5-28 F H CF₃ CH₃ CH₃ 5-29 F H CF₃ CH₃ C₂H₅ 5-30 F H CF₃ CH₃ ^(i)C₃H₇ 5-31 F H CF₃ CH₃ ^(i)C₄H₉ 5-32 F H CF₃ CH₃ CH₂CH═CH₂ 5-33 F H CF₃ CH₃ CH(CH₃)CH═CH₂ 5-34 F H CF₃ CH₃ CH₂C≡CH 5-35 F H CF₃ CH₃ CH(CH₃)C≡CH 5-36 H H CF₂Cl H CH₃ 5-37 H H CF₂Cl H C₂H₅ 5-38 H H CF₂Cl H ^(i)C₃H₇ 5-39 H H CF₂Cl H ^(n)C₃H₇ 5-40 H H CF₂Cl H ^(i)C₄H₉ 5-41 H H CF₂Cl H CH₂CH═CH₂ 5-42 H H CF₂Cl H CH(CH₃)CH═CH₂ 5-43 H H CF₂Cl H CH₂C≡CH 5-44 H H CF₂Cl H CH(CH₃)C≡CH 5-45 F H CF₂Cl H CH₃ 5-46 F H CF₂Cl H C₂H₅ 5-47 F H CF₂Cl H ^(i)C₃H₇ 5-48 F H CF₂Cl H ^(n)C₃H₇ 5-49 F H CF₂Cl H ^(i)C₄H₉ 5-50 F H CF₂Cl H CH₂CH═CH₂ 5-51 F H CF₂Cl H CH(CH₃)CH═CH₂ 5-52 F H CF₂Cl H CH₂C≡CH 5-53 F H CF₂Cl H CH(CH₃)C≡CH 5-54 H H CF₃ H CH₃ 5-55 H H CF₃ H C₂H₅ 5-56 H H CF₃ H ^(i)C₃H₇ 5-57 H H CF₃ H ^(n)C₃H₇ 5-58 H H CF₃ H ^(i)C₄H₉ 5-59 H H CF₃ H CH₂CH═CH₂ 5-60 H H CF₃ H CH(CH₃)CH═CH₂ 5-61 H H CF₃ H CH₂C≡CH 5-62 H H CF₃ H CH(CH₃)C≡CH 5-63 F H CF₃ H CH₃ 5-64 F H CF₃ H C₂H₅ 5-65 F H CF₃ H ^(i)C₃H₇ 5-66 F H CF₃ H ^(i)C₄H₉ 5-67 F H CF₃ H CH₂CH═CH₂ 5-68 F H CF₃ H CH(CH₃)CH═CH₂ 5-69 F H CF₃ H CH₂C≡CH 5-70 F H CF₃ H CH(CH₃)C≡CH 5-71 H CH₃ CF₃ H CH₃ 5-72 H CH₃ CF₃ H C₂H₅ 5-73 H CH₃ CF₃ H ^(i)C₃H₇ 5-74 H CH₃ CF₃ H ^(n)C₃H₇ 5-75 H CH₃ CF₃ H ^(i)C₄H₉ 5-76 H CH₃ CF₃ H CH₂CH═CH₂ 5-77 H CH₃ CF₃ H CH(CH₃)CH═CH₂ 5-78 H CH₃ CF₃ H CH₂C≡CH 5-79 H CH₃ CF₃ H CH(CH₃)C≡CH 5-80 F CH₃ CF₃ H CH₃ 5-81 F CH₃ CF₃ H C₂H₅ 5-82 F CH₃ CF₃ H ^(i)C₃H₇ 5-83 F CH₃ CF₃ H ^(i)C₄H₉ 5-84 F CH₃ CF₃ H CH₂CH═CH₂ 5-85 F CH₃ CF₃ H CH(CH₃)CH═CH₂ 5-86 F CH₃ CF₃ H CH₂C≡CH 5-87 F CH₃ CF₃ H CH(CH₃)C≡CH

The physical properties (melting point, m.p.) or ¹H-NMR (250 or 300 MHz, CDCl₃, TMS, δ(ppm)) data for some of the present compounds are shown below.

Compound 1-332, m.p. 97.0° C.

Compound 1-335, m.p. 80.8° C.

Compound 1-337, m.p. 91.5° C.

Compound 1-338, m.p. 86.1° C.

Compound 1-344, m.p. 94.2° C.

Compound 1-347, m.p. 80.7° C.

Compound 1-350, 2.41 (3H, q, J=1.8 Hz), 4.05-4.35 (2H, b), 6.87-6.94 (1H, m), 7.03 (1H, d, J=2.4 Hz), 7.33 (1H, d, J=8.5 Hz), 7.98 (1H, s)

Compound 1-353, m.p. 124.0° C.

Compound 1-367, 2.44 (3H, q, J=1.9 Hz), 3.04 (3H, s), 6.88 (1H, s), 7.37 (1H, d, J=9.0 Hz), 7.79 (1H, d, J=7.0 Hz), 8.01 (1H, s)

Compound 1-369, 2.44 (3H, q, J=2.0 Hz), 4.57 (2H, s), 7.06 (1H, s), 7.38 (1H, d, J=9.0 Hz), 7.83 (1H, d, J=6.9 Hz), 8.01 (1H, s)

Compound 1-391, m.p. 177.6° C.

Compound 1-392, m.p. 172.5° C.

Compound 1-398, m.p. 133.1° C.

Compound 1-420, 1.25 (3H, t, J=7.5 Hz), 1.51 (3H, d, J=7.0 Hz), 2.42 (3H, q, J=1.8 Hz), 4.0-4.18 (3H, m), 4.82 (1H, d, J=7.9 Hz), 6.59 (1H, d, J=6.3 Hz), 7.23 (1H, d, J=9.3 Hz), 7.97 (1H, s)

Compound 1-429, 1.40 (6H, d, J=6.3 Hz), 2.43 (3H, q, J=2.4 Hz), 4.52-4.63 (1H, m), 7.14 (0.5H, d, J=2.4 Hz), 7.17 (0.5H, d, J=2.4 Hz), 7.24 (1H, d, J=3.6 Hz), 7.29 (1H, s), 7.46 (1H, d, J=8.4 Hz)

Compound 1-439, m.p. 110.6° C.

Compound 1-449, 1.29 (3H, t, J=7.5 Hz), 2.42 (3H, q, J=2.4 Hz), 4.28 (2H, q, J=7.5 Hz), 4.73 (2H, s), 7.20-7.32 (2H, m), 7.49 (1H, d, J=10.4 Hz), 8.00 (1H, s)

Compound 1-456, 1.70 (3H, d, J=6.9 Hz), 2.41 (3H, q, J=2.1 Hz), 3.77 (3H, s), 4.81 (1H, q, J=6.9 Hz), 7.21-7.28 (2H, m), 7.47 (1H, d, J=8.7 Hz), 7.99 (1H, s)

Compound 1-474, m.p. 110.6° C.

Compound 1-475, 1.46 (3H, t, J=5.8 Hz), 2.44 (3H, q, J=1.5 Hz), 4.07 (2H, q, J=5.8 Hz), 6.94 (1H, d, J=5.0 Hz), 7.29 (1H, d, J=7.5 Hz), 8.01 (1H, s)

Compound 1-476, 1.38 (6H, d, J=6.3 Hz), 2.43 (3H, q, J=2.0 Hz), 4.47 (1H, m), 6.99 (1H, d, J=5.0 Hz), 7.29 (1H, d, J=9.5 Hz), 8.00 (1H, s)

Compound 1-482, m.p. 79.8° C.

Compound 1-483, m.p. 132.7° C.

Compound 1-486, m.p. 140.7° C. (decomp.)

Compound 1-487, m.p. 114.1° C.

Compound 1-491, m.p. 82.9° C.

Compound 1-495, m.p. 80.4° C.

Compound 1-496, m.p. 102.0° C.

Compound 1-497, m.p. 82.9° C.

Compound 1-498, m.p. 75.6° C.

Compound 1-499, 0.88 (3H, t, J=7 Hz), 1.2-1.4 (4H, m), 1.55-1.70 (2H, m), 2.43 (3H, q, J=2 Hz), 4.19 (2H, t, J=7 Hz), 4.68 (2H, s), 6.98 (1H, d, J=7 Hz), 7.33 (1H, d, J=8 Hz), 7.99 (1H, s)

Compound 1-500, 1.26 (6H, d, J=6.3 Hz), 2.43 (3H, q, J=2Hz), 4.65 (2H, s), 5.05-5.18 (1H, m), 6.98 (1H, d, J=7 Hz), 7.33 (1H, d, J=8 Hz), 7.98 (1H, s)

Compound 1-501, 1.5-1.9 (8H, m), 2.43 (3H, q, J=2 Hz), 4.65 (2H, s), 5.2-5.4 (1H, m), 6.97 (1H, d, J=7 Hz), 7.33 (1H, d, J=8 Hz), 7.98 (1H, s)

Compound 1-503, 1.68 (3H, d, J=7 Hz), 2.43 (3H, q, J=2 Hz), 3.76 (3H, s), 4.73 (1H, q, J=7 Hz), 6.98 (1H, d, J=7 Hz), 7.32 (1H, d, J=8 Hz), 7.99 (1H, s)

Compound 1-504, 1.25 (3H, t, J=7.3 Hz), 1.68 (3H, d, J=6.8 Hz), 2.42 (3H, q, J=2.0 Hz), 4.21 (2H, q, J=7.3 Hz), 4.70 (1H, q, J=6.8 Hz), 6.99 (1H, d, J=6.8 Hz). 7.32 (1H, d, J=9.3 Hz), 7.98 (1H, s)

Compound 1-511, m.p. 110.7° C.

Compound 1-518, m.p. 131.2° C. (decomp.)

Compound 1-576, 2.43 (3H, q, J=1.8 Hz), 3.67 (2H, s), 3.72 (3H, s), 7.32 (1H, d, J=8.5 Hz), 7.59 (1H, d, J=7.1 Hz), 8.2 (1H, s)

Compound 1-577, 1.15 (3H, t, J=7.5 Hz), 2.36 (3H, q, J=1.8 Hz), 3.58 (2H, s), 4.09 (2H, q, J=7.5 Hz), 7.28 (1H, d, J=8.6 Hz), 7.52 (1H, d, J=7.1 Hz), 7.93 (1H, s)

Compound 1-579, m.p. 71.6° C.

Compound 1-581, m.p. 97.5° C.

Compound 1-584, 1.53 (3H, d, J=7.2 Hz), 2.43 (3H, q, J=1.8 Hz), 3.66 (3H, s), 3.88 (1H, q, J=7.2 Hz), 7.38 (1H, d, J=9.6 Hz), 7.66 (1H, d, J=7.5 Hz), 7.99 (1H, s)

Compound 1-585, 1.17 (3H, t, J=6.9 Hz), 1.53 (3H, d, J=7.2 Hz), 2.43 (3H, q, J=1.8 Hz), 3.89 (1H, q, J=7.2 Hz), 4.11 (2H, q, J=6.9 Hz), 7.37 (1H, d, J=9.6 Hz), 7.67 (1H, d, J=9.0 Hz), 7.99 (1H, s)

Compound 1-586, 0.85 (3H, t, J=6.8 Hz), 1.51-1.62 (5H, m), 2.43 (3H, q, J=1.8 Hz), 3.89 (1H, q, J=7.2 Hz), 4.02 (2H, t, J=6.8 Hz), 7.33 (1H, d, J=9.5 Hz), 7.66 (1H, d, J=7.5 Hz), 7.98 (1H, s)

Compound 1-587, 0.88 (3H, t, J=7.2 Hz), 1.30-1.40 (2H, m), 1.47-1.55 (5H, m), 2.43 (3H, q, J=1.8 Hz), 3.89 (1H, q, J=7.1 Hz), 4.02-4.08 (2H, m), 7.36 (1H, d, J=9.4 Hz), 7.66 (1H, d, J=7.5 Hz), 7.99 (1H, s)

Compound 1-619, 2.45 (3H, q, J=1.6 Hz), 7.60 (1H, d, J=8.6 Hz), 7.80-7.86 (1H, m), 8.04 (1H, s), 8.36 (1H, d, J=2.5 Hz)

Compound 1-621, 1.40 (3H, t, J=7.1 Hz), 2.43 (3H, q, J=1.8 Hz), 4.41 (2H, q, J=7.1 Hz), 7.56 (1H, d, J=8.6 Hz), 7.72-7.78 (1H, m), 8.02 (1H, s), 8.16 (1H, d, J=2.7 Hz)

Compound 1-625, 1.39 (6H, d, J=6.2 Hz), 2.43 (3H, q, J=1.6 Hz), 5.23-5.28 (1H, m), 7.54 (1H, d, J=8.7 Hz), 7.70-7.76 (1H, m), 8.02 (1H, s), 8.10 (1H, d, J=2.6 Hz)

Compound 1-632, m.p. 76.1° C.

Compound 1-637, m.p. 102.8° C.

Compound 1-641, 2.43 (3H, q, J=2.0 Hz), 3.92 (3H, s), 7.39 (1H, d, J=9.5 Hz), 8.02 (1H, s), 8.07 (1H, d, J=7.7 Hz)

Compound 1-642, 1.39 (3H, t, J=7.2 Hz), 2.44 (3H, q, J=1.9 Hz), 4.40 (2H, q, J=7.2 Hz), 7.38 (1H, d, J=9.5 Hz), 8.00-8.06 (2H, m)

Compound 1-981, m.p. 87.1° C.

Compound 1-987, 4.0-4.4 (2H, b), 6.8-6.9 (1H, m), 7.04 (1H, d, J=2.4 Hz), 7.28 (1H, q, J=1.2 Hz), 7.35 (1H, d, J=8.6 Hz), 8.02 (1H, d, J=2.2 Hz)

Compound 1-1025, 5.92 (1H, s), 7.16 (0.5H, d, J=2.4 Hz), 7.19 (0.5H, d, J=2.4 Hz), 7.30 (1H, q, J=1.1 Hz), 7.34 (1H, d, J=5.7 Hz), 7.43 (1H, d, J=9.0 Hz), 8.04 (1H, q, J=3.0 Hz)

Compound 1-1028, m.p. 180.2° C., 5.65-5.9 (1H, br), 7.09 (1H, d, J=7 Hz), 7.27-7.30 (2H, m), 8.10 (1H, q, J=2.2 Hz)

Compound 1-1029, 7.09 (1H, d, J=6.4 Hz), 7.31 (1H, q, J=1.1 Hz), 7.42 (1H, d, J=8.8 Hz), 8.04 (1H, q, J=2.2 Hz)

Compound 1-1035, m.p. 61.1° C.

Compound 1-1057, m.p. 158° C.

Compound 1-1066, m.p. 89.1° C.

Compound 1-1076, m.p. 113.5° C.

Compound 1-1086, m.p. 83.9° C.

Compound 1-1093, m.p. 83.1° C.

Compound 1-1113, m.p. 68.6° C.

Compound 1-1123, m.p. 147.4° C.

Compound 1-1124, m.p. 117.2° C.

Compound 1-1133, m.p. 149.2° C. (decomp.)

Compound 1-1140, m.p. 99.1° C.

Compound 1-1141, m.p. 80.2° C.

Compound 1-1213, m.p. 85.8° C.

Compound 1-1214, m.p. 65.1° C.

Compound 1-1221, 1.54 (3H, d, J=7.2 Hz), 3.66 (3H, s), 3.90 (1H, q, J=7.2 Hz), 7.31 (1H, s), 7.39 (1H, d, J=9.0 Hz), 7.67 (1H, d, J=8.7 Hz), 8.04 (1H, d, J=3.6 Hz)

Compound 1-1222, 1.16 (3H,t, J=5.1 Hz), 1.53 (3H, d, J=7.2 Hz), 3.89 (1H, q, J=7.2 Hz), 4.10 (2H, q, J=5.1 Hz), 7.30 (1H, q, J=1.1 Hz), 7.38 (1H, d, J=9.0 Hz), 7.68 (1H, d, J=7.5 Hz), 8.04 (1H, q, J=2.2 Hz)

Compound 1-1226, 1.12 (3H, d, J=6.0 Hz), 1.21 (3H, d, J=6.0 Hz), 1.52 (3H, d, J=3.0 Hz), 3.88 (1H, q, J=3.0 Hz), 4.85-5.03 (1H, m), 7.30 (1H, q, J=1.8 Hz), 7.37 (1H, d, J=9.0 Hz), 7.67 (1H, d, J=7.5 Hz), 8.02 (1H, q, J=2.1 Hz)

Compound 1-1256, 7.35 (1H, q, J=1.1 Hz), 7.62 (1H, d, J=8.7 Hz), 7.82-7.88 (1H, m), 8.09 (1H, d, J=2.2 Hz), 8.35 (1H, d, J=2.6 Hz)

Compound 1-1258, 1.41 (3H, t, J=7.1 Hz), 4.42 (2H, q, J=7.1 Hz), 7.31 (1H, s), 7.57 (1H, d, J=8.7 Hz), 7.74-7.79 (1H, m), 8.07 (1H, q, J=2.1 Hz), 8.16 (1H, d, J=2.6 Hz)

Compound 1-1269, m.p. 89.7° C.

Compound 1-1274, m.p. 154.2° C.

Compound 1-1278, m.p. 128.6° C.

Compound 1-1279, 1.40 (3H, t, J=7.1 Hz), 4.40 (2H, q, J=7.1 Hz), 7.33 (1H, q, J=1.1 Hz), 7.39 (1H, d, J=9.4 Hz), 8.05 (1H, d, J=8.3 Hz), 8.07 (1H, s)

Compound 1-1346, 2.48 (3H, s), 5.66 (1H, s), 7.08 (1H, d, J=7.8 Hz), 7.28 (1H, d, J=9.0 Hz), 7.32 (1H, s)

Compound 1-1431, m.p. 74.5° C.

Compound 1-1441, m.p. 128.2° C.

Compound 1-1442, 1.73 (3H, d, J=6.6 Hz), 2.49 (3H, q, J=1.3 Hz), 2.54 (1H, d, J=2.0 Hz), 4.84 (1H, m), 7.22 (1H, d, J=6.5 Hz), 7.28-7.34 (2H, m)

Compound 1-1451, 1.29 (3H, t, J=7.0 Hz), 2.47 (3H, q, J=1.4 Hz), 4.27 (2H, q, J=7.0 Hz), 4.68 (2H, s), 6.99 (1H, d, J=7.1 Hz), 7.32 (1H, s), 7.34 (1H, d, J=7.2 Hz)

Compound 1-1458, 1.69 (3H, d, J=6.8 Hz), 2.48 (3H, q, J=1.3 Hz), 3.76 (3H, s), 4.74 (1H, q, J=6.8 Hz), 7.01 (1H, d, J=6.5 Hz), 7.29-7.34 (2H, m)

Compound 1-1540, 1.17 (3H, t, J=7.0 Hz), 1.54 (3H, d, J=7.3 Hz), 2.48 (3H, q, J=1.4 Hz), 3.89 (1H, q, J=7.3 Hz), 4.11 (2H, q, J=7.0 Hz), 7.31 Hz), (1H, s), 7.37 (1H, d, J=9.5 Hz), 7.67 (1H, d, J=7.5 Hz)

Compound 1-1617, m.p. 105.7° C.

Compound 1-1622, 1.27 (3H, t, J=7.0 Hz), 2.42 (3H, q, J=2.0 Hz), 3.26 (0.3H, d, J=7.6 Hz), 3.32 (0.7H, d, J=7.6 Hz), 3.49 (0.7H, d, J=7.6 Hz), 3.54 (0.3H, d, J=7.6 Hz), 4.23 (2H, q, J=7.0 Hz), 4.54 (0.5H, d, J=7.6 Hz), 4.57 (0.5H, d, J=7.6 Hz), 7.34 (1H, d, J=9.3 Hz), 7.40 (1H, d, J=7.5 Hz), 8.00 (1H, s)

Compound 1-1627, m.p. 182.2° C.

Compound 1-1638, 3.66 (2H, s), 7.31 (1H, s), 7.34 (1H, d, J=9.3 Hz), 7.62 (1H, d, J=7.2 Hz), 8.08 (1H, s)

Compound 1-1639, m.p. 158.9° C. (decomp.)

Compound 1-1641, 1.55 (3H, d, J=7.2 Hz), 3.88 (1H, q, J=7.2 Hz), 7.32 (1H, s), 7.37 (1H, d, J=9.2 Hz), 7.69 (1H, d, J=7.1 Hz), 8.03 (1H, s)

Compound 1-1650, 1.11 (3H, t, J=7.5 Hz), 2.03-2.12 (2H, m), 2.43 (3H, q, J=1.8 Hz), 3.75 (3H, s), 4.58 (1H, t, J=7.5 Hz), 6.92 (1H, d, J=8.2 Hz), 7.32 (1H, d, J=9.3 Hz), 8.00 (1H, s)

Compound 1-1655, m.p. 119.7° C., 1.29 (3H, t, J=7.1 Hz), 2.43 (3H, q, J=1.8 Hz), 4.26 (2H, q, J=7.1 Hz), 4.68 (2H, s), 6.91 (1H, s), 7.60 (1H, s), 7.99 (1H, s)

Compound 1-1663, m.p. 136.2° C., 2.44 (3H, q, J=1.8 Hz), 2.58 (1H, t, J=2.3 Hz), 4.78 (2H, d, J=2.3 Hz), 7.12 (1H, s), 7.59 (1H, s), 8.01 (1H, s)

Compound 1-1665, 1.23 (3H, t, J=6.9 Hz), 1.68 (3H, d, J=6.8 Hz), 2.42 (3H, q, J=1.8 Hz), 4.1-4.3 (2H, m), 4.72 (1H, q, J=6.8 Hz), 6.90 (1H, s), 7.58 (1H, s), 7.97 (1H, s)

Compound 1-1670, m.p. 118.1° C.

Compound 1-1673, m.p. 107.2° C.

Compound 1-1678, m.p. 164.7° C.

Compound 1-1679, 1.73 (3H, d, J=6.9 Hz), 2.54 (1H, d, J=2.1 Hz), 4.73-4.90 (1H, m), 7.20 (1H, d, J=6.3 Hz), 7.30 (1H, s), 7.49 (1H, d, J=8.7 Hz), 8.00 (1H, s)

Compound 1-1680, m.p. 90.1° C.

Compound 1-1681, m.p. 148.1° C.

Compound 1-1682, m.p. 107.0° C.

Compound 1-1683, 1.25 (3H, t, J=7.2 Hz), 1.68 (3H, d, J=6.8 Hz), 2.42 (3H, q, J=1.5 Hz), 4.13-4.26 (2H, m), 4.70 (1H, q, J=6.8 Hz), 6.96 (1H, d, J=6.3 Hz), 7.48 (1H, d, J=9.0 Hz), 7.97 (1H, s)

Compound 1-1687, m.p. 200.1° C.

Compound 1-1689, m.p. 76.3° C.

Compound 1-1690, m.p. 196.1° C.

Compound 1-1691, 3.06 (3H, s), 7.10-7.30 (1H, b), 7.30 (1H, s), 7.64 (1H, s), 7.74 (1H, s), 8.06 (1H, q, J=2.1 Hz)

Compound 1-1701, 1.39 (3H, t, J=7.1 Hz), 4.40 (2H, q, J=7.1 Hz), 7.33 (1H, q, J=1.1 Hz), 7.69 (1H, s), 7.97 (1H, s), 8.06 (1H, q, J=2.2 Hz)

Compound 1-1718, m.p. 63.9° C.

Compound 1-1719, m.p. 189.5° C.

Compound 1-1720, m.p. 117.3° C.

Compound 1-1721, m.p. 156.1° C.

Compound 1-1722, 2.47 (3H, q, J=1.8 Hz), 3.05 (3H, s), 7.15-7.30 (1H, b), 7.66 (1H, s), 7.78 (1H, s), 8.03 (1H, s)

Compound 1-1732, 1.38 (3H, t, J=7.1 Hz), 2.44 (3H, q, J=1.8 Hz), 4.39 (2H, q, J=7.1 Hz), 7.68 (1H, s), 7.96 (1H, s), 8.02 (1H, s)

Compound 1-1748, 1.38 (6H, d,J=6.0 Hz), 2.44 (3H, q, J=1.9 Hz), 4.40-4.59 (1H, m), 6.95 (1H, s), 7.55 (1H, s), 8.00 (1H, s)

Compound 1-1780, m.p. 76.4° C.

Compound 1-1781, 3.51 (3H, s), 3.51 (3H, s), 7.30 (1H, q, J=1.2 Hz), 7.59 (1H, d, J=6.7 Hz), 7.65 (1H, d, J=9.0 Hz), 8.06 (1H, d, J=2.1 Hz)

Compound 1-1782, 3.03 (3H, s), 7.09 (1H, s), 7.32 (1H, q, J=1.0 Hz), 7.53 (1H, d, J=8.7 Hz), 7.77 (1H, d, J=6.8 Hz), 8.07 (1H, q, J=2.2 Hz)

Compound 1-1783, 1.38 (6H, d, J=6.1 Hz), 2.43 (3H, q, J=1.7 Hz), 4.4-4.6 (1H, m), 6.95 (1H, d, J=6.4 Hz), 7.47 (1H, d, J=8.9 Hz), 8.00 (1H, s)

Compound 1-1785, 2.43 (3H, q, J=1.9 Hz), 3.03 (3H, s), 7.03 (1H, s), 7.52 (1H, d, J=8.8 Hz), 7.76 (1H, d, J=6.9 Hz), 8.02 (1H, s)

Compound 1-1789, m.p. 78.3° C.

Compound 1-1790, m.p. 63.2° C.

Compound 1-1879, 2.42 (3H, q, J=1.8 Hz), 5.38 (2H, s), 7.28-7.47 (5H, m), 7.56 (1H, d, J=8.7 Hz), 7.72-7.79 (1H, m), 8.00 (1H, s), 8.18 (1H, d, J=2.5 Hz)

Compound 1-1881, 2.20 (0.75H, s), 2.24 (2.25H, s), 2.42 (3H, q, J=1.9 Hz), 3.82 (0.75H, s), 3.98 (2.25H, s), 7.47-7.68 (3H, m), 8.00 (1H, s)

Compound 1-1901, m.p. 99.2° C.

Compound 1-1908, m.p. 77.6° C.

Compound 1-1910, m.p. 75.3° C.

Compound 1-1930, m.p. 139.7° C.

Compound 1-2051, 1.25 (3H, t, J=7.2 Hz), 2.42 (3H, q, J=1.9 Hz), 4.17 (2H, q, J=7.2 Hz), 4.71 (2H, s), 4.82 (2H, s), 7.10 (1H, d, J=6.3 Hz), 7.33 (1H, d, J=9.1 Hz), 7.99 (1H, s)

Compound 1-2054, 1.24 (3H, t, J=7.1 Hz), 1.51 (3H, d, J=7.2 Hz), 2.42 (3H, q, J=1.8 Hz), 4.15 (2H, q, J=7.1 Hz), 4.78 (2H, s), 5.19 (1H, q, J=7.2 Hz), 7.08 (1H, d, J=6.3 Hz), 7.32 (1H, d, J=9.1 Hz), 7.98 (1H, s)

Compound 2-203, 2.3-2.4 (1H, m), 2.35 (3H, q, J=1.9 Hz), 4.5-4.7 (4H, m), 7.00 (1H, d, J=6.5 Hz), 7.19 (1H, m), 7.39 (1H, d, J=2.5 Hz), 7.95 (1H, s)

Compound 2-251, m.p. 168.3° C.

Compound 2-328, 0.90 (3H, t, J=7.3 Hz), 1.54 (3H, d, J=7.0 Hz), 1.70-1.90 (2H, m), 2.46 (3H, m), 4.50 (1H, m), 7.18 (1H, d, J=5.75 Hz), 7.35 (1H, d, J=8.8 Hz), 8.04 (1H, s)

Compound 2-583, m.p. 149.1° C.

Compound 2-631, m.p. 168.3° C.

Compound 2-708, 0.90 (3H, t, J=7.3 Hz), 1.55 (3H, d, J=7.0 Hz), 1.75-1.95 (2H, m), 4.50 (1H, m), 7.22 (1H, d, J=5.8 Hz), 7.30-7.40 (2H, m), 8.08 (1H, q, J=2.2 Hz)

Compound 2-821, m.p. 162.7° C.

Compound 3-139, m.p. 88.2° C.

Compound 4-434, 1.67 (3H, s), 2.35 (3H, q, J=1.7 Hz), 3.0-3.2 (1H, m), 3.4-3.7 (1H, m), 3.71 (3H, s), 7.03 (1H, d, J=5.0 Hz), 7.97 (1H, q, J=3.3 Hz)

Compound 4-451, 1.53 (6H, s), 2.43 (3H, q, J=1.9 Hz), 2.96 (1H, d, J=16.2 Hz), 3.08 (1H, d, J=16.2 Hz), 7.07 (1H, d, J=9.9 Hz), 7.99 (1H, s)

Compound 4-452, 1.4-1.5 (3H, m), 2.43 (3H, q, J=2.0 Hz), 2.7-3.0 (1H, m), 3.1-3.5 (1H, m), 3.5-3.8 (2H, m), 7.07 (1H, d, J=10.0 Hz), 8.00 (1H, q, J=2.5 Hz)

The following will describe formulation examples, in which the present compounds are designated by their compound numbers shown in Tables 1 to 5 and parts are by weight.

FORMULATION EXAMPLE 1

Fifty parts of each of compounds 1-1 to 1-2157, 2-1 to 2-950, 3-1 to 3-582, 4-1 to 4-936, and 5-1 to 5-87, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate, and 45 parts of synthetic hydrated silicon oxide are well pulverized and mixed to give a wettable powder for each compound.

FORMULATION EXAMPLE 2

Ten parts of each of compounds 1-1 to 1-2157, 2-1 to 2-950, 3-1 to 3-582, 4-1 to 4-936, and 5-1 to 5-87, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 35 parts of xylene, and 35 parts of cyclohexanone are well mixed to give an emulsifiable concentrate for each compound.

FORMULATION EXAMPLE 3

Two parts of each of compounds 1-1 to 1-2157, 2-1 to 2-950, 3-1 to 3-582, 4-1 to 4-936, and 5-1 to 5-87, 2 parts of synthetic hydrated silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite, and 64 parts of kaoline clay are well pulverized and mixed, to which water is added, and the mixture is well kneaded, granulated, and dried to give a granule for each compound.

FORMULATION EXAMPLE 4

Twenty-five parts of each of compounds 1-1 to 1-2157, 2-1 to 2-950, 3-1 to 3-582, 4-1 to 4-936, and 5-1 to 5-87, 50 parts of 10% aqueous polyvinyl alcohol solution, and 25 parts of water are mixed, and the mixture is pulverized until the average particle size becomes 5 μm or less to give a flowable for each compound.

FORMULATION EXAMPLE 5

Five parts of compound 1-1650 is added to 40 parts of 10% aqueous polyvinyl alcohol solution and dispersed by emulsion with a homogenizer until the mean particle size becomes 10 μm or less, to which 55 parts of water is added to give a concentrated emulsion.

The following test examples will demonstrate that the present compounds are useful as active ingredients of herbicides. The present compounds are designated by their compound numbers shown in Tables 1 to 5.

The herbicidal activity and phytotoxicity were evaluated at 6 levels with indices of 0 to 5, i.e., designated by the numeral “0”, “1”, “2”, “3”, “4” or “5”, wherein “0” means that there was no or little difference in the degree of germination or growth between the treated and the untreated test plants at the time of examination, and “5” means that the test plants died complete or their germination or growth was completely inhibited. The herbicidal activity is excellent when rated at “4” or “5” but insufficient when rated at “3” or lower. The phytotoxicity is no problematic on practical use when rated at “0” or “1” but not allowed when rated at “2” or higher.

Test Example 1

Foliar Treatment on Upland Fields

Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were filled with soil, in which the seeds of entireleaf morningglory (Ipomoea hederacea var. integriuscula) and velvetleaf (Abutilon theophrasti) were sowed, and the test plants were grown in a greenhouse for 19 days. Each of the test compounds listed below was formulated into an emulsifiable concentrate according to Formulation Example 2, which was diluted with water containing a spreading agent to a prescribed concentration. The dilution was uniformly sprayed over the foliage of the test plants with a sprayer at a volume of 1000 liters per hectare. After the application, the test plants were grown in the greenhouse for 19 days, and the herbicidal activity was examined. The results are shown in Table 6.

TABLE 6 Application amount of Herbicidal activity Test active ingredient Entireleaf compound (g/ha) morningglory Velvetleaf 1-332 500 5 5 1-335 500 5 5 1-338 500 5 5 1-347 500 5 5 1-350 500 5 5 1-353 500 5 5 1-367 500 5 5 1-369 500 5 5 1-391 500 5 5 1-392 500 5 5 1-398 500 5 5 1-420 500 5 5 1-429 500 5 5 1-439 500 5 5 1-449 500 5 5 1-456 500 5 5 1-474 500 5 5 1-475 500 5 5 1-476 500 5 5 1-482 500 5 5 1-483 500 5 5 1-486 500 5 5 1-487 500 5 5 1-491 500 5 5 1-495 500 5 5 1-496 500 5 5 1-497 500 5 5 1-498 500 5 5 1-499 500 5 5 1-500 500 5 5 1-501 500 5 5 1-503 500 5 5 1-504 500 5 5 1-511 500 5 5 1-576 500 5 5 1-577 500 5 5 1-579 500 5 5 1-581 500 5 5 1-584 500 5 5 1-585 500 5 5 1-586 500 5 5 1-587 500 5 5 1-619 500 5 5 1-621 500 5 5 1-625 500 5 5 1-637 500 5 5 1-641 500 5 5 1-642 500 5 5 1-987 500 5 5 1-1025 500 5 5 1-1028 500 5 5 1-1029 500 5 5 1-1035 500 5 5 1-1057 500 5 5 1-1066 500 5 5 1-1076 500 5 5 1-1086 500 5 5 1-1093 500 5 5 1-1113 500 5 5 1-1123 500 5 5 1-1124 500 5 5 1-1133 500 5 5 1-1140 500 5 5 1-1141 500 5 5 1-1213 500 5 5 1-1214 500 5 5 1-1221 500 5 5 1-1222 500 5 5 1-1226 500 5 5 1-1274 500 5 5 1-1278 500 5 5 1-1279 500 5 5 1-1422 500 5 5 1-1431 500 5 5 1-1441 500 5 5 1-1451 500 5 5 1-1458 500 5 5 1-1540 500 5 5 1-1617 500 5 5 1-1622 500 5 5 1-1627 500 5 5 1-1638 500 5 5 1-1639 500 5 5 1-1641 500 5 5 1-1650 500 5 5 1-1655 500 5 5 1-1663 500 5 5 1-1665 500 5 5 1-1670 500 5 5 1-1673 500 5 5 1-1678 500 5 5 1-1679 500 5 5 1-1680 500 5 5 1-1681 500 5 5 1-1682 500 5 5 1-1683 500 5 5 1-1691 500 5 5 1-1701 500 5 5 1-1718 500 5 5 1-1719 500 5 5 1-1722 500 5 5 1-1732 500 5 5 1-1748 500 5 5 1-1780 500 5 5 1-1781 500 5 5 1-1782 500 5 5 1-1783 500 5 5 1-1785 500 5 5 2-203 500 5 5 2-251 500 5 5 2-328 500 5 5 2-583 500 5 5 2-631 500 5 5 2-708 500 5 5 2-821 500 5 5 3-139 500 5 5 4-434 500 5 5 4-451 500 5 5 1-344 2000 5 5 1-981 2000 5 5 1-1689 2000 5 5 1-1720 2000 5 5 1-1721 2000 5 5

Test Example 2

Foliar Treatment on Upland Fields

Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were filled with soil, in which the seeds of barnyardgrass (Echinochloa crus-galli), entireleaf morningglory (Ipomoea hederacea var. integriuscula), and velvetleaf (Abutilon theophrasti) were sowed, and the test plants were grown in a greenhouse for 19 days. Each of the test compounds listed below was formulated into an emulsifiable concentrate according to Formulation Example 2, which was diluted with water containing a spreading agent to a prescribed concentration. The dilution was uniformly sprayed over the foliage of the test plants with a sprayer at a volume of 1000 liters per hectare. After the application, the test plants were grown in the greenhouse for 19 days, and the herbicidal activity was examined. The results are shown in Table 7.

TABLE 7 Application amount of Herbicidal activity Test active ingredient Barnyard- Entireleaf Velvet- compound (g/ha) grass morningglory leaf 1-369 32 5 5 5 1-420 32 5 5 5 1-439 32 4 5 5 1-482 32 5 5 5 1-486 32 4 5 5 1-487 32 5 5 5 1-491 32 5 5 5 1-495 32 5 5 5 1-496 32 5 5 5 1-499 32 5 5 5 1-503 32 5 5 5 1-576 32 5 5 5 1-577 32 5 5 5 1-579 32 5 5 5 1-581 32 5 5 5 1-584 32 5 5 5 1-585 32 5 5 5 1-625 32 5 5 5 1-641 32 5 5 5 1-642 32 5 5 5 1-1057 32 5 5 5 1-1076 32 4 5 5 1-1123 32 4 5 5 1-1124 32 5 5 5 1-1140 32 5 5 5 1-1141 32 4 5 5 1-1213 32 5 5 5 1-1214 32 5 5 5 1-1221 32 5 5 5 1-1222 32 5 5 5 1-1226 32 5 5 5 1-1279 32 5 5 5 1-1422 32 5 5 5 1-1431 32 5 5 5 1-1441 32 5 5 5 1-1458 32 5 5 5 1-1540 32 5 5 5 1-1665 32 5 5 5 1-1670 32 5 5 5 1-1673 32 5 5 5 1-1678 32 5 5 5 1-1679 32 5 5 5 1-1680 32 5 5 5 1-1681 32 5 5 5 1-1682 32 5 5 5 1-1683 32 5 5 5 1-1701 32 5 5 5 1-1732 32 5 5 5 1-1780 32 5 5 5 1-1783 32 5 5 5 2-203 32 4 5 5 2-251 32 5 5 5 2-583 32 4 5 5 2-631 32 5 5 5 2-821 32 5 5 5 4-434 32 5 5 5

Test Example 3

Soil Surface Treatment on Upland Fields

Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were filled with soil, in which the seeds of entireleaf morningglory (Ipomoea hederacea var. integriuscula) and velvetleaf (Abutilon theophrasti) were sowed. Each of the test compounds listed below was formulated into an emulsifiable concentrate according to Formulation Example 2, which was diluted with water to a prescribed concentration. The dilution was uniformly sprayed over the soil surface in the pots with a sprayer at a volume of 1000 liters per hectare. After the application, the test plants were grown in a greenhouse for 19 days, and the herbicidal activity was examined. The results are shown in Table 8.

TABLE 8 Application amount of Herbicidal activity Test active ingredient Entireleaf compound (g/ha) morningglory Velvetleaf 1-347 500 5 5 1-332 500 5 5 1-335 500 5 5 1-338 500 5 5 1-353 500 5 5 1-367 500 5 5 1-369 500 5 5 1-391 500 5 5 1-392 500 5 5 1-398 500 5 5 1-420 500 5 5 1-439 500 5 5 1-449 500 5 5 1-456 500 5 5 1-474 500 5 5 1-475 500 5 5 1-476 500 5 5 1-482 500 5 5 1-486 500 5 5 1-487 500 5 5 1-491 500 5 5 1-495 500 5 5 1-496 500 5 5 1-497 500 5 5 1-498 500 5 5 1-499 500 5 5 1-500 500 5 5 1-501 500 5 5 1-503 500 5 5 1-504 500 5 5 1-511 500 5 5 1-576 500 5 5 1-577 500 5 5 1-579 500 5 5 1-581 500 5 5 1-584 500 5 5 1-585 500 5 5 1-587 500 5 5 1-621 500 5 5 1-625 500 5 5 1-641 500 5 5 1-642 500 5 5 1-1028 500 5 5 1-1029 500 5 5 1-1035 500 5 5 1-1057 500 5 5 1-1066 500 5 5 1-1076 500 5 5 1-1093 500 5 5 1-1113 500 5 5 1-1123 500 5 5 1-1124 500 5 5 1-1133 500 5 5 1-1140 500 5 5 1-1141 500 5 5 1-1213 500 5 5 1-1214 500 5 5 1-1221 500 5 5 1-1222 500 5 5 1-1226 500 5 5 1-1279 500 5 5 1-1422 500 5 5 1-1431 500 5 5 1-1441 500 5 5 1-1451 500 5 5 1-1458 500 5 5 1-1540 500 5 5 1-1617 500 5 5 1-1622 500 5 5 1-1627 500 5 5 1-1638 500 5 5 1-1639 500 5 5 1-1641 500 5 5 1-1650 500 5 5 1-1655 500 5 5 1-1663 500 5 5 1-1665 500 5 5 1-1670 500 5 5 1-1673 500 5 5 1-1678 500 5 5 1-1679 500 5 5 1-1680 500 5 5 1-1681 500 5 5 1-1682 500 5 5 1-1683 500 5 5 1-1691 500 5 5 1-1780 500 5 5 1-1781 500 5 5 1-1782 500 5 5 1-1783 500 5 5 1-1785 500 5 5 2-203 500 5 5 2-251 500 5 5 2-328 500 5 5 2-583 500 5 5 2-631 500 5 5 2-708 500 5 5 2-821 500 5 5 4-434 500 5 5

Test Example 4

Flooding Treatment on Paddy Fields

Cylindrical plastic pots of 9 cm in diameter and 11 cm in depth were filled with soil, in which the seeds of barnyardgrass (Echinochloa oryzicola) were sowed. These pots were flooded to form a paddy field, and the test plants were grown in a greenhouse for 7 days. Each of the test compounds listed below was formulated into an emulsifiable concentrate according to Formulation Example 2, which was diluted with water to a prescribed concentration. The dilution was applied to the water surface in the pots at a volume of 50 liters per hectare. After the application, the test plants were grown in the greenhouse for 19 days, and the herbicidal activity was examined. The results are shown in Table 9.

TABLE 9 Application amount of Test active ingredient Herbicidal activity compound (g/ha) Barnyardgrass 1-332 250 5 1-335 250 5 1-338 250 5 1-347 250 5 1-353 250 5 1-367 250 5 1-369 250 5 1-391 250 5 1-392 250 5 1-398 250 5 1-420 250 5 1-439 250 5 1-449 250 5 1-456 250 5 1-474 250 5 1-475 250 5 1-476 250 5 1-482 250 5 1-483 250 5 1-486 250 5 1-487 250 5 1-491 250 5 1-495 250 5 1-496 250 5 1-497 250 5 1-498 250 5 1-499 250 5 1-500 250 5 1-501 250 5 1-503 250 5 1-504 250 5 1-511 250 5 1-576 250 5 1-577 250 5 1-579 250 5 1-581 250 5 1-584 250 5 1-585 250 5 1-586 250 5 1-587 250 5 1-621 250 5 1-625 250 5 1-641 250 5 1-642 250 5 1-1025 250 5 1-1028 250 5 1-1029 250 5 1-1035 250 5 1-1057 250 5 1-1066 250 5 1-1076 250 5 1-1086 250 5 1-1093 250 5 1-1113 250 5 1-1123 250 5 1-1124 250 5 1-1133 250 5 1-1140 250 5 1-1141 250 5 1-1213 250 5 1-1214 250 5 1-1221 250 5 1-1222 250 5 1-1226 250 5 1-1274 250 5 1-1278 250 5 1-1279 250 5 1-1422 250 5 1-1431 250 5 1-1441 250 5 1-1451 250 5 1-1458 250 5 1-1540 250 5 1-1617 250 5 1-1622 250 5 1-1627 250 5 1-1638 250 5 1-1639 250 5 1-1641 250 5 1-1650 250 5 1-1655 250 5 1-1663 250 5 1-1665 250 5 1-1670 250 5 1-1673 250 5 1-1678 250 5 1-1679 250 5 1-1680 250 5 1-1681 250 5 1-1682 250 5 1-1683 250 5 1-1687 250 5 1-1691 250 5 1-1701 250 5 1-1718 250 5 1-1719 250 5 1-1722 250 5 1-1732 250 5 1-1748 250 5 1-1780 250 5 1-1781 250 5 1-1782 250 5 1-1783 250 5 1-1785 250 5 2-203 250 5 2-251 250 5 2-328 250 5 2-583 250 5 2-631 250 5 2-708 250 5 2-821 250 5 3-139 250 5 4-434 250 5 4-451 250 5 1-344 500 5 1-1690 500 5 1-1720 500 5 1-1721 500 5

Test Example 5

Foliar Treatment on Upland Fields

Plastic pots of 25×18 cm² in area and 7 cm in depth were filled with soil, in wghich the seeds of soybean (Glycine max), corn (Zea mays), entireleaf morningglory (Ipomoea hederacea var. intefriscula), common cocklebur (Xanthium pensylvanicum), common ragweed (Ambrosia artemisiifolia), and common lanbsquarters (Chenopodium album), were sowed, and the test plants were grown for 16 days. Each of the test compounds listed below was formulated into an emulsifiable concentrate according to Formulation Example 2, which was diluted with water to a prescribed concentration. The dilution was uniformly sprayed over the foliage of the test plants with a sprayer at a volume of 1000 liters per hectare. At this time, the unfavorable weeds and crop plants, although their growth state was different depending upon the weed species, were at the 1- to 4leaf stage, and the plant height was 5 to 20 cm. After 18 days from the application, the herbicidal activity and phytoxicity were examined. The results are shown in Table 10. This test was made in a greenhouse over the entire period.

TABLE 10 Application amount of Herbicidal activity and phytotoxicity active Entireleaf Common Test ingredient Soy- Common morning- Common lamb- compound (g/ha) Corn bean cocklebur glory ragweed squarters 1-495 63 1 1 5 5 5 5 1-496 63 1 1 5 5 5 5 1-499 63 1 1 5 5 5 4 1-503 63 1 2 5 5 5 5 1-577 63 1 2 5 5 5 5

Test Example 6

Foliar Treatment on Upland Fields

Plastic pots of 16×11 cm² in are and 7 cm in depth were filled with soil, in which the seeds of wheat (Triticum aestivum), pale smartweed (Polygonum lapathifolium), catchweed bedstraw (Galium aparine), and common chickweed (Stellaria media) were sowed, and the test plants were grown for 29 days. Each of the test compounds listed below was formulated into an emulsifiable concentrate according to Formulation Example 2, which was diluted with water to a prescribed concentration. The dilution was uniformly sprayed over the foliage of the test plants with a sprayer at a volume of 1000 liters per hectare. At this time, the unfavorable weeds and crop plants, although their growth state was different depending upon the weed species, were at the 1- to 4-leaf stage, and the plant height was 5 to 15 cm. After 25 days from the application, the herbicidal activity and phytotoxicity were examined. The results are shown in Table 11. This test was made in a greenhouse over the entire period.

TABLE 11 Application amount of Herbicidal activity and phytotoxicity active Pale Catch- Common Test ingredient smart- weed chick- compound (g/ha) Wheat weed bedstraw weed 1-439  63 1 5 5 5 1-482  63 1 5 5 5 1-486  63 1 5 5 5 1-496  63 0 4 5 4 1-1076 63 1 5 5 5 1-1123 63 1 5 5 5 1-1441 63 1 5 5 5

Test Example 7

Soil Surface Treatment on Upland Fields

Plastic pots of 25×18 cm² in area and 7 cm in depth were filled with soil, in which the seeds of soybean (Glycine max), corn (Zea mays), common lambsquarters (Chenopodium album), slender amaranth (Amaranthus gracilis), and pale smartweed (Polygonum lapathifolium) were sowed. Each of the test compounds listed below was formulated into an emulsifiable concentrate according to Formulation Example 2, which was diluted with water to a prescribed concentration. The dilution was uniformly sprayed over the soil surface in the pots with a sprayer at a volume of 1000 liters per hectare. After the application, the test plants were grown in a greenhouse for 19 days, and the herbicidal activity and phytotoxicity were examined. The results are shown in Table 12.

TABLE 12 Application amount of Herbicidal activity and phytotoxicity active Common Pale Test ingredient Soy- lamb- Slender smart- compound (g/ha) bean Corn squarters amaranth weed 1-511  63 1 0 5 5 5 1-642  63 1 0 5 5 5 1-1279 63 0 1 5 5 5 1-1691 63 0 1 5 5 5 2-203  63 2 2 5 5 5 2-631  63 1 3 5 5 5 

What is claimed is:
 1. A compound of the formula:

wherein R³ is hydrogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, or C₁-C₃ alkoxy C₁-C₃ alkyl, and Q¹ is [Q¹-1], of the formula:

wherein X is hydrogen or halogen; Y is halogen, nitro, cyano, or trifluoromethyl; B¹ is hydrogen, halogen, nitro, cyano, OR²⁷, SR²⁷, SO₂OR²⁷, NR¹¹(R¹²), SO₂NR¹¹((R¹²), NR¹¹(COR¹³), NR¹¹(SO₂R¹⁴), N(SO₂R¹⁴)(SO₂R¹⁵), N(SO₂R¹⁴)—(COR¹³), NHCOOR¹³, COOR²⁷, CONR¹¹(R¹²), CSNR¹¹(R¹²), CR¹⁷═CR¹⁸COOR¹³, CR¹⁷═CR¹⁸CONR¹¹(R¹²), CH₂CHWCOOR¹³, CH₂CHWCONR¹¹(R¹²), CR¹⁷═N—OR³³, CR¹⁷═NNR¹¹(R¹²), CR¹⁷(Z²R³⁴)₂, OCO₂R¹⁹; or OCOR¹⁹; wherein R²⁷ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₈ cycloalkyl, benzyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, cyano C₃-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-C₈ alkylthioalkyl, carboxy C₁-C₆ alkyl, (C₁-C₈ alkoxy)carbonyl C₃-C₆ alkyl, (C₃-C₆ haloalkoxy)carbonyl C₃-C₆ alkyl, {(C₃-C₄ alkoxy) C₃-C₄ alkoxy}carbonyl C₃-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₃-C₆ alkyl, CH₂CO—N(R¹¹)R¹², CH₂COON(R¹¹)R¹², CH(C₃-C₄ alkyl)CON(R¹¹)R¹², CH(C₁-C₄ alkyl) COON(R¹¹)R¹², {(C₃-C₆ alkoxy)carbonyl C₃-C₆ alkyl}oxycarbonyl C₁-C₆ alkyl, or hydroxy C₃-C₆ alkyl; R¹¹ and R¹² are independently hydrogen, C₃-C₆ alkyl, C₃-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, cyano C₃-C₆ alkyl, C₂-C₈ alkoxyalkyl, C₂-C₈ alkylthioalkyl, carboxy C₃-C₆ alkyl, (C₁-C₆ alkoxy)carbonyl C₃-C₆ alkyl, (C₃-C₈ cycloalkoxy)carbonyl C₃-C₆ alkyl, {(C₃-C₄ alkoxy) C₃-C₄ alkoxy}carbonyl C₃-C₆ alkyl, or R¹¹ and R¹² are combined together to form tetramethylene, pentamethylene, or ethyleneoxy-ethylene; R¹³ is hydrogen, C₃-C₆ alkyl, C₃-C₆ haloalkyl, C₃-C₈ cycloalkyl, or C₃-C₆ alkenyl; R¹⁴ and R¹⁵ are independently C₁-C₆ alkyl, C₁-C₆ haloalkyl, or phenyl optionally substituted with methyl or nitro; R¹⁷ and R¹⁸ are independently hydrogen or C₃-C₆ alkyl; R¹⁹ is C₁-C₆ alkyl; R³³ is hydrogen, C₃-C₆ alkyl, C₃-C₆ haloalkyl, C₃-C₈ cycloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, C₃-C₆ haloalkynyl, cyano C₁-C₆ alkyl, or (C₃-C₆ alkoxy)carbonyl C₃-C₆ alkyl; R³⁴ is C₃-C₆ alkyl, or two R³⁴'s are combined together to form (CH₂)₂ or (CH₂)₃ and; W is hydrogen, chlorine, or bromine. 